著者

松居 隆 大塚 幸 酒井 浄

出版者

公益社団法人日本薬学会

雑誌

藥學雜誌 (ISSN:00316903)

巻号頁・発行日

vol.120, no.10, pp.825-837, 2000-10-01

被引用文献数

1

---

One century has passed since fugu toxin was named tetrodotoxin (TTX) by Tahara. Chemical problems such as crystallization of tetrodotoxin and subsequent structure determination were solved by research groups headed by Tsuda, Hirata, Woodward, and Mosher. The International Symposium on the Chemistry of Natural Products in Kyoto (1964) was well known as symposium which the structure of TTX was internationally clarified. Since the first isolation of toxin from taricha torosa (imori) as natural source except for fugu fishes, distribution of toxin in nature has been widely investigated. And, it was proved that toxin is not produced by fugu fishes, but rather is formed by sea bacteria (30 sp.) such as Alteromonas sp, Vibrio sp, Shewanella. However, it seems to be difficult to explain the tetrodotoxin accumulation at high concentration in fugu by only toxin production by bacteria. TTX analogues were isolated from natural origins such as crabs, fish, annelids, and algae. Based on the structure of these toxin analogues, the biosynthesis of toxin and the structure-activity relationship (Na^+ channel) were proposed by Yasumoto-Yamashita. The findings of wide distribution of toxin in nature may be attributed to development of highly sensitive detection method for toxin. The interesting proposal for the biosynthesis and the structure activity, and the detection method for toxin are outlined in this review.

著者

末宗 洋 原部 哲治 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.9, pp.3632-3637, 1988-09-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

23 30

---

Two trihydroxy unsaturated C-18 fatty acids [(9S, 12S, 13S)-trihydroxyoctadeca-10E, 15Z-dienoic acid (methyl ester) and (9S, 12S, 13S)-trihydroxy-10E-octadecenoic acid (methyl ester)] isolated from rice plants as agents with activity against blast disease were synthesized from (+)-dimethyl tartrate.

著者

樫原 宏 末宗 洋 常広 菜穂美 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.9, pp.2581-2582, 1990-09-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

2 3

---

The enones (II), which were obtained from dimethyl 4, 5-isopropylidenedioxy-2-oxopentylphosphonate (Ia) and various aldehydes, were easily converted to 2-alkenylfurans (III) by treatment with p-TsOH in MeOH. In a similar manner, the furfuryl phosphonate (IVa) and the 3-methylfurfuryl phosphonate (IVb) were obtained from Ia and its 3-methylated analogue (Ib), respectively.

著者

樫原 宏 末宗 洋 藤本 勝彦 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.10, pp.2610-2614, 1989-10-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

7 9

---

A new synthetic route to optically active α, β-, β', γ'-unsaturated alcohols was established. The chiral enones (6 and 8), prepared from dimethyl malate via chiral phosphonates (4 and 5), were diastereoselectively reduced with Zn(BH4)2 to afford the 1, 3-syn derivatives (9 and 11). As an application of this 1, 3-asymmetric induction, the fungitoxic C-18 hydroxy unsaturated fatty acid isolated from stromata of Epichloe typhina was synthesized.

著者

松居 隆 大塚 幸 酒井 浄

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.120, no.10, pp.825-837, 2000-10-01 (Released:2008-05-30)

参考文献数

36

被引用文献数

4 11

---

One century has passed since fugu toxin was named tetrodotoxin (TTX) by Tahara. Chemical problems such as crystallization of tetrodotoxin and subsequent structure determination were solved by research groups headed by Tsuda, Hirata, Woodward, and Mosher. The International Symposium on the Chemistry of Natural Products in Kyoto (1964) was well known as symposium which the structure of TTX was internationally clarified. Since the first isolation of toxin from taricha torosa (imori) as natural source except for fugu fishes, distribution of toxin in nature has been widely investigated. And, it was proved that toxin is not produced by fugu fishes, but rather is formed by sea bacteria (30 sp.) such as Alteromonas sp, Vibrio sp, Shewanella. However, it seems to be difficult to explain the tetrodotoxin accumulation at high concentration in fugu by only toxin production by bacteria. TTX analogues were isolated from natural origins such as crabs, fish, annelids, and algae. Based on the structure of these toxin analogues, the biosynthesis of toxin and the structure-activity relationship (Na+ channel) were proposed by Yasumoto-Yamashita. The findings of wide distribution of toxin in nature may be attributed to development of highly sensitive detection method for toxin. The interesting proposal for the biosynthesis and the structure activity, and the detection method for toxin are outlined in this review.

著者

酒井 浄

出版者

公益社団法人 日本薬学会

雑誌

ファルマシア (ISSN:00148601)

巻号頁・発行日

vol.35, no.10, pp.1072, 1999-10-01 (Released:2018-08-26)

著者

酒井 浄

出版者

公益社団法人 日本薬学会

雑誌

ファルマシア (ISSN:00148601)

巻号頁・発行日

vol.26, no.8, pp.795-797, 1990-08-01 (Released:2018-08-26)

著者

酒井 浄

出版者

公益社団法人 日本薬学会

雑誌

ファルマシア (ISSN:00148601)

巻号頁・発行日

vol.20, no.10, pp.990-991, 1984-10-01 (Released:2018-08-26)

著者

/ 船越 和久 末宗 洋 大石 武 秋田 弘幸 酒井 浄 Kiyoshi Sakai

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.34, no.7, pp.3058-3060, 1986-07-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

7 9

---

Microbial reduction of 7-methoxycarbonyl bicyclo[4. 3. 0]non-3-en-8-one ((±)-3) afforded the optically active (-)-3, which was efficiently converted by ring contraction using thallium (III) nitrate to the intermediate (11) used to synthesize carbacyclin (1).

著者

末宗 洋 田中 正一 尾葉石 浩 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.1, pp.15-21, 1988-01-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

9 18

---

Synthesis of prostaglandin A2 (PGA2) by means of a route involving enzymatic reactions is described. Enantioselective reduction and hydrolysis of trans-3, 4-bis(methoxycarbonyl)cyclopentanone (1) were examined using yeasts or enzymes, and it was found that (+)- and (-)-1 are easily obtained by an enzymatic procedure. Compound (+)-1 was converted to the Corey intermediate for PGA2 via the regioselective hydrolysis of the (+)-diacetate (8) with porcine pancreatic lipase. This synthesis based on the enzymatic approach was proved to be useful for the synthesis of both PGA and PGE from (-)-1.

著者

末宗 洋 明石 アイリ 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.3, pp.1055-1061, 1985-03-25 (Released:2008-03-31)

参考文献数

17

被引用文献数

4 7

---

Chemical synthesis of platelet-activating factor (PAF, 1) and its enantiomer was studied. Several alkoxymethyl alkenyl ketones (5a-c, n=14 or 16) were synthesized from Wittig-Horner reagents (4, n=14 or 16) with cyclohexanecarboxaldehyde, octylaldehyde, and benzaldehyde, and subjected to asymmetric reduction with BINAL-H1) which is known to show high enantioselectivity in the reduction of enones. Optical purities of the reduction products (6) were determined from the 400 MHz proton nuclear magnetic resonance spectra after conversion of 6 to the esters (9) of optically active α-methoxy-α-trifluoromethyl-phenylacetic acid (MTPA). The MTPA ester of (+)-6b showed high optical purity (80%ee). Upon oxidative cleavage of the double bond with ozone followed by reduction with NaBH4, the acetate of (+)-6b afforded two known compounds (11 and 12), which have previously been transformed into natural PAF (1).

著者

末宗 洋 肥塚 美千代 鎌下 知子 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.5, pp.1379-1381, 1989-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

15 21

---

γ-Hydroxyethyl α, β-unsaturated γ-lactone (2) is a promising intermediate for the synthesis of eldanolide and cis, cis-1, 2, 3-trisubstituted cyclopentane, which could be converted to 11-deoxyprostaglandins. In order to prepare optically active 2, enzymatic hydrolysis of (±)-trans-cyclohexene-4, 5-diacetate with Pseudomonas fluorescens lipase was examined, and the monoalcohol ((-)-6, >99%ee)with R-configuration was obtained in accored with prediction based on the three-site model proposed by us. Compound (-)-6 could be converted to the chiral lactone ((-)-2) via a sequence of reactions involving ring cleavage.

著者

肥塚 美千代 方 成林 末宗 洋 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.5, pp.1185-1187, 1989-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

9 12

---

1, 4-Addition of organocopper reagents to γ-substituted α, β-unsaturated γ-lactones followed by intramolecular trapping of the resulted enolates afforded cis, cis-1, 2, 3-trisubstituted cyclopentanes and cyclohexanes in a stereocontrolled manner. This new cyclization reaction to cyclopentanes provides a new synthetic route to the key intermediate in the synthesis of 11-deoxyprostaglandins.

著者

肥塚 美千代 林 教行 鎌下 知子 末宗 洋 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.4, pp.1550-1553, 1988-04-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

13 14

---

2, 6-Dioxabicyclo[3.3.0]octan-3, 7-dione seems to be a promising compound for the synthesis of natural products such as epoxyeicosatrienoic acid, laurediol, and eldanolide. This compound, consisting of two γ-lactones, could be prepared by double lactonization of the silver salt of trans-3-hexenedioic acid using iodine. Starting with this bis-lactone, (±)-eldanoide could by synthesized in a stereocontrolled manner.

著者

末宗 洋 林 教行 舟越 和久 秋田 弘幸 大石 武 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.5, pp.2168-2170, 1985-05-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

24 29

---

(S)-13-Hydroxy-9Z, 11E-octadecadienoic acid, a defensive substance in rice, was synthesized with high enantioselectivity by the reduction of the corresponding ketone with yeasts.

著者

酒井 浄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.51, no.8, pp.733-743, 1993-08-01 (Released:2009-11-16)

参考文献数

41

被引用文献数

11 13

---

Rh (I) -catalyzed cyclization of substituted 4-pentenals into cyclopentanones found first by our laboratory was developed into the highly diastereoselective and enantioselective asymmetric cyclization by using the Rh (I) -complex with chiral ligand such as BINAP, and (+) -DIPMC. Cationic Rh (I) with BINAP afforded the best asymmetric cyclization in chemical yields and enantioselectivity as well as the diastereoselectivity. This cyclization method could be successfully applied for the synthesis of iridomyrmecin and isoiridomyrmecin from (-) -i-monene. In addition, Rh (I) -catalyzed cyclization of oct-6-enal with the cis-cyclohexane-1, 2-dioxy function at C 3-position afforded two conformational diastereomers due to a cis-cyclohexane-1, 2-diol moiety. The interesting findings found by our group are summarized as main topics in this paper.

著者

樫原 宏 末宗 洋 常広 菜穂美 酒井 浄

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.9, pp.2581-2582, 1990-09-25

---

The enones (II), which were obtained from dimethyl 4,5-isopropylidenedioxy-2-oxopentylphosphonate (Ia) and various aldehydes, were easily converted to 2-alkenylfurans (III) by treatment with p-TsOH in MeOH. In a similar manner, the furfuryl phosphonate (IVa) and the 3-methylfurfuryl phosphonate (IVb) were obtained from Ia and its 3-methylated analogue (Ib), respectively.

著者

岡野 耕二 水原 由加子 末宗 洋 秋田 弘幸 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.4, pp.1358-1365, 1988-04-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

5 10

---

During a detailed examination on the cyclization of 1, 4-diketones to cyclopentenones, we have found that two oxygenated products (4 and 5) are formed when the purification by column chromatography on silica gel takes a long time. The highly functionalized cyclopentenone (4a) obtained as the major product in this manner seems to be an attractive synthon for the synthesis of natural products. For eaxmple, the chiral synthon (1S, 4S)-4-benzyloxycarbonyl-1, 4-dihydroxy-2-methoxycarbonyl-3-methyl-2-cyclopentene ((+)-7) with high optical purity was obtained by microbial reduction with Rhodotorula rubra CCY 20-7-1, and the absolute stereochemistry was established independently by using the exciton chirality method and the chemical method.

著者

末宗 洋 水原 由加子 秋田 弘幸 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.34, no.8, pp.3440-3444, 1986-08-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

24 44

---

An enzymatic synthesis of 2, 3-O-isopropylidene-sn-glycerol (10), the synthetic key intermediate for platelet-activating factor, was achieved. Several 1, 3-di-O-acyl-2-benzylglycerols (5a-d) were synthesized from dihydroxyacetone dimer (2), and subjected to enzyme-catalyzed asymmetric hydrolysis. The optical purities of the mono-hydrolyzed products (6) were determined from the 400 MHz proton nuclear magnetic resonance spectra after conversion of 6 to the esters of (-)α-methoxy-α-trifluoromethylphenylacetic acid. Upon hydrogenolysis of the benzyl ether, followed by protection of diol and hydrolysis of the acetate, (-)-6a afforded 10.

著者

上野 貢嗣 末宗 洋 佐伯 清太郎 酒井 浄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.9, pp.4021-4025, 1985-09-25 (Released:2008-03-31)

参考文献数

13

被引用文献数

10 15

---

The conversion of naturally abundant (+)-limonen-10-ol (2) into the synthetic intermediate (3) for brefeldin A is described. The cis-3, 4-disubstituted cyclopentanone (4), which was easily obtained from 2 by Rh (I)-catalyzed cyclization reaction via the 4-pentenal derivative, could be converted to the target compound 3 via the appropriate modification of substituents on the five-membered ring.