Total synthesis of a piperidine alkaloid, microcosamine A

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, intramolecula...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (1), p.251-258
Main Authors: Raji Reddy, Chada, Latha, Bellamkonda, Warudikar, Kamalkishor, Singarapu, Kiran Kumar
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02085a