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

Brian N. Laforteza; Mark Pickworth; David W.C. MacMillan

doi:10.1002/anie.201305171

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

Brian N. Laforteza, Mark Pickworth, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

78 Scopus citations

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.

Original language	English (US)
Pages (from-to)	11269-11272
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	43
DOIs	https://doi.org/10.1002/anie.201305171
State	Published - Oct 18 2013

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

alkaloids
enantioselectivity
natural products
organocatalysis
total synthesis

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10.1002/anie.201305171

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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.",

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AU - Pickworth, Mark

AU - MacMillan, David W.C.

PY - 2013/10/18

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KW - natural products

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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