☆ 4.8 Article

Integral Stereocontrolled Synthesis of a Spiro-norlignan, Sequosempervirin A: Revision of Absolute Configuration

ORGANIC LETTERS (2011)

期刊

ORGANIC LETTERS

卷 13, 期 17, 页码 4640-4643

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol2018533

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Chemistry, Organic

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Ministry of Education, Culture, Sports, Science and Technology of Japan

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摘要

A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, In which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydroxyl group at the 8-position. The absolute configuration of natural sequosempervirin A was revised to be 4S based on this synthesis.

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