Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction

Michael J. Di Maso; Gabriella M. Nepomuceno; Michael A. St. Peter; Haley H. Gitre; Kevin S. Martin; Jared T. Shaw

doi:10.1021/acs.orglett.6b00413

Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction

Michael J. Di Maso, Gabriella M. Nepomuceno, Michael A. St. Peter, Haley H. Gitre, Kevin S. Martin, Jared T. Shaw

Chemistry

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

7 Scopus citations

Abstract

Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.

Original language	English (US)
Pages (from-to)	1740-1743
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.6b00413
State	Published - Apr 15 2016

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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title = "Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction",

abstract = "Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.",

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AU - Di Maso, Michael J.

AU - Nepomuceno, Gabriella M.

AU - St. Peter, Michael A.

AU - Gitre, Haley H.

AU - Martin, Kevin S.

AU - Shaw, Jared T.

PY - 2016/4/15

Y1 - 2016/4/15

N2 - Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.

AB - Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.

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