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Synthesis and enzymatic cyclization of (3S)-14-fluoro-2,3-oxidosqualene

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
51
Identifiers
DOI: 10.1016/s0040-4039(98)02197-2

Abstract

Abstract A convergent asymmetric synthesis led to ( 3S)-14-fluoro-2,3-oxidosqualene (14-FOS, 16), which was cyclized by bacterial squalene:hopane cyclase to a monocarbocyclic product with a bridged ether and a 2:3 mixture of bicyclic alcohols. 14-FOS was neither a substrate nor an inhibitor for vertebrate oxidosqualene:lanosterol cyclase.

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