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...

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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
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creator Evans, Gary B
Cameron, Scott A
Culbert, Shayne R
Grant, Peter K
description 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.
doi_str_mv 10.1016/j.tetlet.2014.09.068
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subjects Decarboxylation
Formations
Ketones
Methylene
Oxidation
Tetrahedrons
title Convenient syntheses of ring-B-nor analogues of Ambrox registered and amberketal via a novel ring contraction reaction
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