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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Synthesis of Diepoxide Analogues of Fumagillin

WE Harvey and JO Miners

Australian Journal of Chemistry 32(11) 2473 - 2481
Published: 1979

Abstract

Pathways from cyclohexanone to compounds of the general type 4-(1',2'-epoxy-1'-methylalkyl)- 1-oxaspiro[2,5]octane (5), the simplest diepoxide analogues of the antibiotic fumagillin (1a), are described. The sequence involves the initial formation of 6-acetyl-1,4-dioxaspiro[4,5]decane (2a) which is converted into a 2-alkenylcyclohexanone through the Wittig reaction. Subsequent spiro epoxidation of the cyclic ketone and peracid epoxidation of the side chain double bond affords the diepoxides (5a-c). In most respects the synthetic diepoxides possess the same stereochemistry as the equivalent functionality of fumagillin.

https://doi.org/10.1071/CH9792473

© CSIRO 1979

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