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The first total synthesis of (−)-benzomalvin A and benzomalvin B via the intramolecular aza-Wittig reactions

✍ Scribed by Toshiyuki Sugimori; Tomohiro Okawa; Shoji Eguchi; Akikazu Kakehi; Eiji Yashima; Yoshio Okamoto

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
712 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The first total synthesis of(-)-benzomalvin A, which possesses 4(3H)-quinazolinone and 1,4-benzodiazepin-5-one moieties, was described. Both of 6-and 7-membered ring skeletons were efficiently constructed by the intramolecular aza-Wittig reactions as the key reactions. The enantiomeric excess of synthetic (-)-benzomalvin A was more than 99.7 % based on I-IPLC analysis using specially modified cellulose as a stationary phase. Furthermore, investigation on a specific conformational dynamic behavior of(-)-benzomalvin A was carried out by NMR studies and X-ray crystallographic analysis, and benzomalvin B was readily synthesized fi'om (-)-benzomalvin A by only two steps.

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