Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine
(Chemical Equation Presented) We have developed novel asymmetric routes to (-)-9-epi-pentazocine and (-)-aphanorphine from a D-tyrosine derivative. The tricyclic frameworks of (-)-9-epi-pentazocine and (-)-aphanorphine were assembled stereoselectively via intramolecular Friedel-Crafts reaction of the corresponding bicyclic precursors, generated with titanium-promoted enyne cyclization and indium-initiated atom-transfer radical cyclization, respectively.
Yang, Xiaobao,Zhai, Hongbin,Li, Zhong
supporting information; experimental part
p. 2457 - 2460
(2009/05/26)
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