BIOMIMETIC SYNTHESIS OF 12-OXY-PIMARANES FROM 12,13-EPOXY-LABDADIENES

作者: Alejandro F. Barrero , Quintana M. Rafael , Joaquin C. Altarejos

DOI: 10.1016/S0040-4020(01)87113-1

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摘要: Abstract Reactions of methyl 12,13-epoxy-cis-communates ( 3 , 4 ) and 12,13-epoxy-trans-communates 5 ), 6 with BF3:etherate at 0°C are reported. They occur in a stereoselective stereospecific way yielding mainly C-12 oxygenated pimaranes. When the reaction was carried out from two tetracyclic ketones 17 18 were also isolated. Reaction mechanisms stereochemical implications discussed.

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