ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Farnesol (3a) is the precursor to the irregular C12 terpenoid (4S, 4aS, 8aS)-1,2,3,4,4a,5,8,8a-octahydro-4,8a-dimethylnaphthalen-4a-ol (= dehydrogeosmin; 1). The irregular C-backbone originates from the oxidative removal of a C3 side chain from a C15 eudesmane-type intermediate (Scheme 2). The bicyclic C-framework is assembled by a formal addition of H2O across the endocyclic double bonds of a monocyclic germacradiene-type precursor. The biosynthetic pathway follows from administration of the deuteriated farnesols 3b-e to flower heads of the cactaceae Rebutia marsoneri Werd. and mass-spectroscopic analysis of the collected volatiles.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19930760714
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