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SPIRO-ACTIVATED CYCLOPROPANES: VERSATILE INTERMEDIATES FOR THE TOTAL SYNTHESIS OF NATURAL PRODUCTS

A novel approach to natural product synthesis is presented herein which encompasses three original functionalization processes. These are; (a) the direct photochemical conversion of alkenes to spiro-activated cyclopropanes, (b) the homoconjugate addition of organo-magnesium reagents to said cyclopropanes, and (c) the ozonolysis of isopropylidene malonate enolates. An application of this new methodology to the partial synthesis of racemic brefeldin A is then described.

Identiferoai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/15563
Date January 1979
CreatorsLIVINGHOUSE, THOMAS STUART
Source SetsRice University
LanguageEnglish
Detected LanguageEnglish
TypeThesis, Text
Formatapplication/pdf

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