Journal
NATURAL PRODUCT RESEARCH
Volume 23, Issue 3, Pages 256-263Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786410801997075
Keywords
sclareol; cheilanthanes; petrosaspongionolide; oxaziridinium salt
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Funding
- DGRST
- CNRS
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The synthesis of two marine sponge metabolites 5 and 8 from naturally occurring (-)-sclareol is described here. The sesterterpenolide (5) is synthetised for the first time, establishing the absolute configuration of this compound. The key intermediate, aldehyde (10), was obtained from (-)-sclareol in good overall yields. The use of Katsumura's Wittig reagent and subsequent photochemical oxidation delivered the sesterterpenolide (8), which was chemoselectively epoxidized on exocyclic terminal olefin using the oxaziridinium salt (14) and transformed in four steps to carboxylic acid (5).
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