beta-Silyl Styrene As a Dienophile in the Cycloaddition with 3,5-Dibromo-2-pyrone for the Total Synthesis of (+/-)-Pancratistatin

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초록

A new synthetic route to (+/-)-pancratistatin was devised utilizing beta-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone. The TMS group incorporated in the cycloadduct permitted a facile elimination process for the eventual installation of the C(1)-OH function. Subsequent transformations including Curtius rearrangement and Bischler-Napieralski reactions completed the total synthesis of (+/-)-pancratistatin.

키워드

DIELS-ALDER REACTIONANTINEOPLASTIC AGENTSAMARYLLIDACEAE ALKALOIDS(+)-PANCRATISTATINPANCRATISTATINNARCICLASINE(+)-NARCICLASINE(+/-)-CRININE
제목
beta-Silyl Styrene As a Dienophile in the Cycloaddition with 3,5-Dibromo-2-pyrone for the Total Synthesis of (+/-)-Pancratistatin
저자
Jung, Yong-GeunKang, Ho-UngCho, Hyun-KyuCho, Cheon-Gyu
DOI
10.1021/ol202525a
발행일
2011-11
유형
Article
저널명
Organic Letters
13
21
페이지
5890 ~ 5892