title: Terpestacin core structure. control of stereochemistry.
abstract: [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.
authors.affiliation: Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, 96822, USA.
authors.forename: Gideon O
authors.initials: GO
authors.lastname: Berger
authors.forename: Marcus A
authors.initials: MA
authors.lastname: Tius
mesh_terms: D000478:Alkylation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; C080890:terpestacin; C013905:cyclopentenone