著者
豊田 達郎
出版者
京都大学
巻号頁・発行日
1974

論薬博第131号
著者
菅沢 勉 豊田 達郎 笹倉 和幸
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.22, no.4, pp.771-781, 1974-04-25 (Released:2008-03-31)
被引用文献数
6 13

dl-Camptothecin (XXX) and two epimeric N-formyl-1, 2, 6, 7-tetrahydrocamptothecins (XXIIIa, b) have been synthesized from 3-oxo-1H-pyrrolo [3, 4-b] quinoline IIIa by using following two key reactions. 1) An intramolecular aldol condensation of the imido-ester (VIIIb→IXb). 2) Vilsmeier reaction on a 4-methoxy-2-pyridone ring (XVIb→XVII) followed by nucleophilic attack of a malonate carbanion onto the formyl-pyridone ring (XVII→XVIII).
著者
菅沢 勉 笹倉 和幸 豊田 達郎
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.22, no.4, pp.763-770, 1974-04-25 (Released:2008-03-31)
被引用文献数
7 12

A D-E ring analog (XX) of camptothecin (I) was synthesized from 4-methoxy-1-methyl-2 (1H)-pyridone by using Vilsmeier reaction followed by nucleophilic direct introduction of di-tert-butyl malonate onto the pyridone ring, ethylation and hydroxylation.
著者
菅沢 勉 笹倉 和幸 日高 哲郎 豊田 達郎
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.22, no.4, pp.757-762, 1974-04-25 (Released:2008-03-31)
被引用文献数
1 2

Attempted synthesis of 3-substituted (alkoxycarbonyl, hydroxymethyl or cyano)-2, 3-dihydro-2-benzyl (acyl or alkoxycarbonyl)-1H-pyrrolo [3, 4-b] quinolines (II), (III), and (VI) as potential ring A-B-C components for a total synthesis of dl-camptothecin (I) is described.