Enantioselective synthesis of the oxadecalin core of phomactin A via a highly stereoselective Diels-Alder reaction.
Phomactin A (1) is a selective antagonist of platelet activating factor (PAF). Herein, we report our progress toward the construction of the oxadecalin core of 1. This route is based on the Diels-Alder cycloaddition of an appropriately functionalized vinyl pyran and a complementary dienophile. A model of this reaction involving 2 and maleic anhydride was conducted. Adduct 3 contains the correct stereochemical arrangements between functional groups necessary for gaining access to phomactin A. Reaction: see text.
Chemler
S R
SR
Laboratory of Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, Box 106, New York, New York 10021, USA.
Iserloh
U
U
Danishefsky
S J
SJ
D005658:Fungi / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008299:Maleic Anhydrides / Q000737:chemistry; D008956:Models, Chemical; D009281:Naphthalenes / Q000138:chemical synthesis*; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D008299:Maleic Anhydrides; D009281:Naphthalenes; D010972:Platelet Activating Factor; D010975:Platelet Aggregation Inhibitors; C449320:oxadecalin; C413206:phomactin A