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Biosynthesis of the Irregular C 12 ‐Terpenoid Dehydrogeosmin in Flower Heads of Rebutia marsoneri W ERD. ( Cactaceae )
Author(s) -
Feng Zhuofu,
Huber Udo,
Boland Wilhelm
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760714
Subject(s) - chemistry , farnesol , terpenoid , stereochemistry , bicyclic molecule , biosynthesis , double bond , organic chemistry , biochemistry , gene
Farnesol ( 3a ) is the precursor to the irregular C 12 terpenoid (4 S , 4a S , 8a S )‐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 C 3 side chain from a C 15 eudesmane‐type intermediate ( Scheme 2 ). The bicyclic C‐framework is assembled by a formal addition of H 2 O 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.