Transannular Diels-Alder studies on the asymmetric total synthesis of chatancin: The pyranophane approach

Authors
Toro, A L'Heureux, A Deslongchamps, P
Citation
A. Toro et al., Transannular Diels-Alder studies on the asymmetric total synthesis of chatancin: The pyranophane approach, ORG LETT, 2(18), 2000, pp. 2737-2740
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
18
Year of publication
2000
Pages
2737 - 2740
Database
ISI
SICI code
1523-7060(20000907)2:18<2737:TDSOTA>2.0.ZU;2-Q
Abstract
A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcoph ytin linking these tetracycles to cembranoids by a pyranophane transannular Diels-Alder reaction. Preliminary synthetic results in this direction to r each macrocyclic dienedione 28 from farnesol are reported. Major synthetic steps include a Prins reaction, two enantioselective hydrogenations, and a macrocyclization via a beta-ketosulfoxide Michael-addition on an enone.