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Total synthesis of a piperidine alkaloid, microcosamine A
Chada Raji Reddy1, Bellamkonda Latha, Kamalkishor Warudikar
1Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India 500 007. rajireddy@iict.res.in.
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.
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