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Issue 1, 2016
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Total synthesis of a piperidine alkaloid, microcosamine A

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Abstract

The first asymmetric total synthesis of a new natural piperidine alkaloid, microcosamine A, has been accomplished from D-serine and D-methyl lactate as chiral pool starting materials. Key features of the strategy include the utility of Horner–Wadsworth–Emmons reaction, Luche reduction, intramolecular carbamate N-alkylation to form the piperidine framework and Julia–Kocienski olefination to install the triene side-chain.

Graphical abstract: Total synthesis of a piperidine alkaloid, microcosamine A

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Article information


Submitted
08 Oct 2015
Accepted
03 Nov 2015
First published
03 Nov 2015

Org. Biomol. Chem., 2016,14, 251-258
Article type
Paper

Total synthesis of a piperidine alkaloid, microcosamine A

C. Raji Reddy, B. Latha, K. Warudikar and K. K. Singarapu, Org. Biomol. Chem., 2016, 14, 251
DOI: 10.1039/C5OB02085A

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