Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A

Yiqing Feng; Max M. Majireck; Steven M. Weinreb

doi:10.1002/anie.201207949

Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A

Yiqing Feng
, Max M. Majireck
, Steven M. Weinreb

Chemistry

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

27 Scopus citations

Abstract

Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.

Original language	English (US)
Pages (from-to)	12846-12849
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	51
DOIs	https://doi.org/10.1002/anie.201207949
State	Published - Dec 14 2012

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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abstract = "Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.",

author = "Yiqing Feng and Majireck, \{Max M.\} and Weinreb, \{Steven M.\}",

year = "2012",

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AU - Feng, Yiqing

AU - Majireck, Max M.

AU - Weinreb, Steven M.

PY - 2012/12/14

Y1 - 2012/12/14

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AB - Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.

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U2 - 10.1002/anie.201207949

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 51

ER -

Total synthesis of the unusual monoterpenoid indole alkaloid (±)-alstilobanine A

Abstract

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