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Publication Type
Journal Article
UWI Author(s)
Author, Analytic
Martin, G.D.A.; Reynolds, Williams F.; Reese, Paul B.
Author Affiliation, Ana.
Department of Chemistry
Article Title
Stemodane skeletal rearrangement: Chemistry and microbial transformation
Medium Designator
n/a
Connective Phrase
n/a
Journal Title
Phytochemistry
Translated Title
n/a
Reprint Status
n/a
Date of Publication
2005
Volume ID
66
Issue ID
8
Page(s)
901-909
Language
n/a
Connective Phrase
n/a
Location/URL
n/a
ISSN
0031-9422
Notes
n/a
Abstract
Solvolytic rearrangement of the C/D ring system of the tetracyclic diterpenoid stemodinone (2) afforded the compounds 15(13→ 12)abeo-13β-hydroxvstemaran-2-one (5) and 15(8 → 9)abeo- 8β(H)-12β-hyd roxystach an-2- one (10). Terpene 5 possesses a novel diterpene skeleton. Oxidation of these compounds yielded their respective diketones. Bioconversion of 5 by Rhizopus oryzae yielded 15(13→ 12)abeo-7β, 13β-dihydroxystemaran-2-one (18) while microbial transformation of 10 provided 15(8→ 9)abeo-8β(H)-6α,12β-dihydroxystachan-2-one (19) 15(8→ 9)abeo-8β(H)-7β, 12β-dihydroxystachan-2-one (20) and 15(8 → 9)abeo-8β(H)-6α,12β,14β-trihydroxystachan-2-one (21). A rationale for the formation of the rearranged compounds is proposed.....
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Keywords