Transannular Diels-Alder studies on the asymmetric total synthesis of chatancin: the pyranophane approach.
[reaction: see text] A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcophytin linking these tetracycles to cembranoids by a pyranophane transannular Diels-Alder reaction. Preliminary synthetic results in this direction to reach 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.
Toró
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Laboratoire de Synthèse Organique, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Quebec Canada.
L'Heureux
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Deslongchamps
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P
D000818:Animals; D003063:Cnidaria / Q000737:chemistry; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005204:Farnesol / Q000737:chemistry; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
D004224:Diterpenes; D010972:Platelet Activating Factor; C414662:chatancin; D005204:Farnesol