Convenient syntheses of ring-B-nor analogues of Ambrox registered and amberketal via a novel ring contraction reaction

Manool is converted into ring-B-nor analogues of commercially important perfumery compounds via a novel ring-B-nor intermediate methylene ketone 9. Compound 9 is synthesised via the formation of an exocyclic bromonium ion and the concomitant ring contraction of the B-ring of a diterpene skeleton der...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2014-11, Vol.55 (45), p.6227-6230
Main Authors: Evans, Gary B, Cameron, Scott A, Culbert, Shayne R, Grant, Peter K
Format: Article
Language:English
Subjects:
Decarboxylation
Formations
Ketones
Methylene
Oxidation
Tetrahedrons
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Manool is converted into ring-B-nor analogues of commercially important perfumery compounds via a novel ring-B-nor intermediate methylene ketone 9. Compound 9 is synthesised via the formation of an exocyclic bromonium ion and the concomitant ring contraction of the B-ring of a diterpene skeleton derived from manool. Oxidation and base treatment of the ring-contracted product result in dehydrohalogenation and decarboxylation to afford methylene ketone compound 9, which is then converted to ring-B-nor analogues of Ambrox registered and amberketal.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2014.09.068