著者

末宗 洋

出版者

九州大学

巻号頁・発行日

1983

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博士論文

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

末宗 洋

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.42, no.5, pp.482, 2006-05-01 (Released:2018-08-26)

著者

末宗 洋

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.36, no.4, pp.267-269, 2000-04-01 (Released:2018-08-26)

参考文献数

6

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

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.

著者

末宗 洋 岩崎 源司 上野 貢嗣 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.32, no.11, pp.4632-4636, 1984-11-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

2 5

---

The chemical conversion of (+)-limonene (1) and (-)-perillyl alcohol (10) into 9-substituted p-mentha-1, 8 (10)-diene derivatives is described. The lithiated species of 1 and 10 were easily obtained in good yields, by using sec-butyl lithium in N, N, N', N'-tetramethylethylenediamine. The reaction of the lithiated species (A and B) with various electrophiles was completed within 1-2 h to give 9-substituted p-mentha-1, 8 (10)-diene derivatives. The stereochemistry of the chiral center of the starting material was retained in the products. 9-Hydroxy-p-mentha-1, 8 (10)-diene (8) was also obtained by another short sequence of steps. Oxidation of the phenylthio derivative (7) gave the sulfoxide (9). Treatment of 9 with trimethyl phosphite afforded 8.

著者

上野 貢嗣 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.32, no.9, pp.3768-3769, 1984-09-25 (Released:2008-03-31)

参考文献数

3

被引用文献数

4 12

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The key intermediate (11) for the synthesis of carbacyclin (1) was synthesized by the application of a new method for stereoselective five-membered ring formation using Wilkinson complex.

著者

樫原 宏 篠木 浩 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.34, no.11, pp.4527-4532, 1986-11-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

6 11

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During the course of synthetic studies on the 5, 6-disubsituted 4-oxo-tetrahydro-2-pyroneskeleton in connection with biologically active compounds, we have found a convenient procedure for the regioselective introduction of a double bond in methyl alkyl ketones and a novel synthetic method for indan derivatives.