4.8 Article

Double conjugate addition of a nitropropionate ester to a quinone monoketal:: Synthesis of an advanced intermediate to (±)-gelsemine

Journal

ORGANIC LETTERS
Volume 9, Issue 16, Pages 3153-3156

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol071174p

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Funding

  1. NIGMS NIH HHS [R01 GM049093, R01 GM049093-14, R01 GM049093-15, GM-49093] Funding Source: Medline

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[GRAPHICS] 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.

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