Stereoselective Syntheses of Four Diastereomers of 3,9,12-Trihydroxycalamenene via a Benzobicyclo[3.3.1] Intermediate

The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel−Crafts-type Michael addition of α,β-unsa...

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Veröffentlicht in:	Journal of organic chemistry 2010-06, Vol.75 (12), p.4224-4229
Hauptverfasser:	Sun, Yongquan, Yu, Binxun, Wang, Xiaolei, Tang, Shibing, She, Xuegong, Pan, Xinfu
Format:	Artikel
Sprache:	eng
Schlagworte:	Bridged Bicyclo Compounds - chemistry Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemistry Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Terpenes - chemical synthesis Terpenes - chemistry
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Beschreibung
Zusammenfassung:	The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel−Crafts-type Michael addition of α,β-unsaturated lactones.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo1008349