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Total syntheses of (+)-nogarene and (+)-7,8-dihydronogarene

✍ Scribed by Motoji Kawasaki; Fuyuhiko Matsuda; Shiro Terashima

Book ID: 104218553
Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 267 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84471-8

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✦ Synopsis

Total syntheses of the title compounds, the simplest and the hitherto unknown novel nogalamycin congeners, were first accomplished by elaborating the CDEF-ring system (2) from the methyl ketone (5) and subjecting 2 to regioselective Diels-Alder reaction with the bistrimethylsilyl keteneacetal (2_). Nogalamycin (1) and its congeners are notable members of the anthracycline family because of their unique structures and prominent antitumor activities. Especially, 7-con-O-methylnogarol (2) which can be chemically derived from 1, has been reported to exhibit more promising anticancer activity than the parent compound (l_).' j_: x=0

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