1 0 0 0 OA フラン類の分子内Diels-Alder反応における分子設計
- 著者
- 早川 謙二 兼松 顕
- 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.44, no.2, pp.109-117, 1986-02-01 (Released:2009-11-13)
- 参考文献数
- 58
- 被引用文献数
- 6 7
This article reviews the recent advances in the intramolecular Diels-Alder reactions of furans, which include the reactions with furan as a diene (type I), furan as a part of diene (type II), and furan as a dienophile (type III). This review involves the analysis of the important controlling factors in these reactions as well as their application to the natural product synthesis.
- 著者
- 早川 謙二 麻生 和義 大薄 悟 兼松 顕
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.30, pp.387-394, 1988
Intramolecular cycloadditions of Allenes constitute the versatile methods for the stereocontrolled synthesis of variously functionalized polycyclic compounds. Especially, intramoleclar Diels-Alder reactions using allenic dienophiles can full enjoy the merits of the unique structure of allens and proceed with extraordinary ease. On the basis of this strategy, several new synthtic methodologies were developed; (1) the intramolecular Diels-Alder reaction of allenyl ethers followed by hydration andoxidation provided a new polycyclic lactone synthesis (Scheme 1). This method was successfully applied to the total synthesis of platyphyllide 30(Scheme 5). (2) The allenyl ether bearing a substituent at C-2 position (ex.,1c,1d) underwent the tandem [2+2] cycloaddition and [3,3] sigmatropic rearrangement to produce the novel product having an bicyclo [n.3.11 carbon ring system (ex., 5c, 5d) (Scheme 2).
- 著者
- 藤井 郁雄 阿部 昌之 早川 謙二 兼松 顕
- 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.4670-4673, 1984-11-25 (Released:2008-03-31)
- 参考文献数
- 5
- 被引用文献数
- 2 4
3, 4-Dimethoxy trans-6-morphinanone (1) and its cis isomer (2) were prepared stereoselectively from thebaine (3) and dihydrocodeinone (9), respectively. A general way of spectrally differentiating between these two stereoisomers is discussed.
1 0 0 0 OA ペリ環状反応を基盤とする新規複素環合成反応
- 著者
- 早川 謙二
- 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.45, no.1, pp.60-70, 1987-01-01 (Released:2009-11-13)
- 参考文献数
- 41
- 被引用文献数
- 2 3
New approaches to the heterocyclic syntheses through pericyclic reactions are presented in three sections.(1) The utility of (phenylsulfonyl) propadiene (1) as an allenic dienophile and/or electrophile was revealed by its facile intermolecular cycloaddition reactions with electron-rich dienes, tropone, azaheptafulvenes, and thebaine derivatives, which afforded various heterocyclic compounds including some novel ring systems. (2) trans-4- (Phenylsulfinyl) -3-buten-2-one (29) underwent a new versatile addition-elimination (trans-vinylation) reaction with five-membered heterocycles such as furans, pyrroles, imidazole, pyrazole, and 6- (dimethylamino) fulvene to give excellent yields of the corresponding vinylated compounds. This method combined with the intramolecular Diels-Alder reaction was applied to the synthesis of linearly condensed tricyclic heterocycles like psoralen (31) and the novel aza-analogue of psoralen (38). (3) Intramolecular cycloaddition (ex., Diels-Alder reaction) using allenic dienophiles proceeded with extraordinary ease due to their favorable geometry. These reactions were successfully utilized in the development of new polycyclic lactone synthesis, furan ring transfer (FRT) reactions, tandem intramolecular [2+2] -cycloaddition, [3, 3] -sigmatropic rearrangement, and indole synthesis. Application of some of these new methods to the natural products synthesis is also described.