Enantioselective total synthesis of aspidophytine

Shinjiro Sumi; Koji Matsumoto; Hidetoshi Tokuyama; Tohru Fukuyama

doi:10.1021/ol034445e

Enantioselective total synthesis of aspidophytine

Shinjiro Sumi, Koji Matsumoto, Hidetoshi Tokuyama, Tohru Fukuyama

PHA - Molecular Pharmaceutical Science

The University of Tokyo

Research output: Contribution to journal › Article › peer-review

88 Citations (Scopus)

Abstract

(Matrix presented) An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.

Original language	English
Pages (from-to)	1891-1893
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	11
DOIs	https://doi.org/10.1021/ol034445e
Publication status	Published - 2003 May 29

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author = "Shinjiro Sumi and Koji Matsumoto and Hidetoshi Tokuyama and Tohru Fukuyama",

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AU - Sumi, Shinjiro

AU - Matsumoto, Koji

AU - Tokuyama, Hidetoshi

AU - Fukuyama, Tohru

PY - 2003/5/29

Y1 - 2003/5/29

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AB - (Matrix presented) An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.

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JO - Organic Letters

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Enantioselective total synthesis of aspidophytine

Abstract

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