Terpestacin core structure. control of stereochemistry.
[reaction: see text] The alpha-hydroxycyclopentenone core structure of terpestacin has been prepared in a model system through an allene ether Nazarov cyclization of an alkylidene-gamma-butyrolactone followed by regio- and stereoselective alkylation reactions. The stereochemistry at C15 (terpestacin numbering) has been used to control stereochemistry at C1 and at C23. The use of E-alkylidene-gamma-butyrolactones extends the scope of the cationic cyclopentannelation reaction.
Berger
Gideon O
GO
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, 96822, USA.
Tius
Marcus A
MA
D000478:Alkylation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; C080890:terpestacin; C013905:cyclopentenone