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Issue 30, 2012
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Platinum catalyzed 7-endocyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

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Abstract

The scope and limitations of the platinum catalyzed 7-endo cyclization of internal alkynyl amides were investigated. Substitution of the alkyne with an aryl group gave better results, presumably because it stabilized the transition state. Applying the reaction to a secondary amide, the caprazamycin core was successfully synthesized from commercially available material in eight steps.

Graphical abstract: Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

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Article information


Submitted
15 Jan 2012
Accepted
09 Mar 2012
First published
12 Mar 2012

Org. Biomol. Chem., 2012,10, 6074-6086
Article type
Paper

Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

C. Tsukano, S. Yokouchi, A. Girard, T. Kuribayashi, S. Sakamoto, T. Enomoto and Y. Takemoto, Org. Biomol. Chem., 2012, 10, 6074
DOI: 10.1039/C2OB25111F

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