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

✍ Scribed by Brian J. Robustell; Ikuro Abe; Glenn D. Prestwich

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
266 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

πŸ“œ SIMILAR VOLUMES

A convenient synthesis of [3-3H]squalene
A convenient synthesis of [3-3H]squalene and [3-3H]-2,3-oxidosqualene
✍ Maurizio Ceruti; Giorgio Grosa; Flavio Rocco; Franco Dosio; Luigi Cattel πŸ“‚ Article πŸ“… 1994 πŸ› John Wiley and Sons 🌐 French βš– 421 KB

## Abstract [3‐^3^H]Squalene and [3‐^3^H]‐2,3‐oxidosqualene, key compounds for studying the biosynthesis of sterols, were synthesized. The main step was a modified Wittig reaction of [1‐^3^H]trisnorsqualene aldehyde with a phosphorus ylide to give [3‐^3^H]squalene or with a sulfur ylide to give [3‐