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Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

ABSTRACT: A double conjugate addition between the lithium dianion of ethyl 3-nitropropionate and p-benzoquinone dimethyl ketal afforded a mixture of diastereomeric [3.2.1]bicylooctanones. These products were converted into an advanced intermediate previously carried forward to (+/-)-gelsemine by Fukuyama and Liu.

SUBMITTER: Grecian S

PROVIDER: S-EPMC2518665 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

Grecian Scott S Aubé Jeffrey J

Organic letters 20070712 16

A double conjugate addition between the lithium dianion of ethyl 3-nitropropionate and p-benzoquinone dimethyl ketal afforded a mixture of diastereomeric [3.2.1]bicylooctanones. These products were converted into an advanced intermediate previously carried forward to (+/-)-gelsemine by Fukuyama and Liu. ...[more]

PMID: 17628069

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