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Enantioselective total synthesis of (-)-minovincine in nine chemical steps: an approach to ketone activation in cascade catalysis.

ABSTRACT: Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl.

SUBMITTER: Laforteza BN

PROVIDER: S-EPMC3934209 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of (-)-minovincine in nine chemical steps: an approach to ketone activation in cascade catalysis.

Laforteza Brian N BN Pickworth Mark M Macmillan David W C DW

Angewandte Chemie (International ed. in English) 20130902 43

Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl. ...[more]

PMID: 24000234

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