Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin

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• 作者：Takahiro SuzukiSoichiro Watanabe ; Susumu Kobayashi ; Keiji Tanino
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：19
• 期：4
• 页码：922-925
• 全文大小：473K
• ISSN：1523-7052

文摘

(+)-Iso-A82775C is a proposed biosynthetic precursor of the chloropupukeananin family and an important intermediate for related natural products. The first enantioselective total synthesis of (+)-iso-A82775C (18 steps, 2.2% overall yield) toward the eventual biomimetic total synthesis of chloropupukeananin is described. The key steps are (1) the enantioselective Diels–Alder reaction of 4-bromo-3-hydroxy-2-pyrone with methyl 2-chloroacrylate using cinchonine as an organocatalyst and (2) the anti-selective Cu-mediated S_N2′ reaction to afford the axially chiral vinylallene moiety.