Stereospecific synthesis of squalenoid epoxide vinyl ethers as inhibitors of 2,3-oxidosqualene cyclase
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 461-469
- https://doi.org/10.1039/p19880000461
Abstract
The stereospecific synthesis of squalenoid epoxide vinyl ethers with an isopentyloxy group is described. The synthesis involves the preparation of the C22 squalenoid aldehyde bromohydrin (15) by a new method via a one-step cleavage of lipophilic epoxides using periodic acid in diethyl ether, and the preparation of (1-isopentyloxyethyl)diphenylphosphine oxide (24). The structure of this compound has been confirmed by X-ray analysis. The configuration of vinyl ethers, synthesized using a Wittig-Horner reaction, has been determined by 13C n.m.r. Biological results show that vinyl ethers (5) and (27) are competitive inhibitors of 2,3-oxidosqualene cyclase from rat liver.This publication has 3 references indexed in Scilit:
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