Total Synthesis of (-)-Hennoxazole A

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• 作者：Thomas E. Smith ; Wen-Hsin Kuo ; Victoria D. Bock ; Jennifer L. Roizen ; Emily P. Balskus ; Ashleigh B. Theberge
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：March 15, 2007
• 年：2007
• 卷：9
• 期：6
• 页码：1153 - 1155
• 全文大小：80K
• 年卷期：v.9,no.6(March 15, 2007)
• ISSN：1523-7052

文摘

An enantioselective, convergent, total synthesis of the antiviral marine natural product (-)-hennoxazole A has been completed in 17 steps,longest linear sequence, from serine methyl ester and in 9 steps from an achiral bisoxazole intermediate. Elaboration of a thiazolidinethioneallowed for rapid assembly of the pyran-based ring system. Key late-stage coupling was effected by deprotonation of the bisoxazole methylgroup, followed by alkylation with an allylic bromide side chain segment.