Enantiocontrolled synthesis of (+)-aphanorphine from (R)-O-benzylglycidol: assignment of absolute configuration

…, K Inomata, T Sato, K Ogasawara

Index: Takano, Seiichi; Inomata, Kohei; Sato, Tsutomu; Ogasawara, Kunio Journal of the Chemical Society, Chemical Communications, 1989 , # 21 p. 1591 - 1592

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Citation Number: 10

Abstract

Aphanorphine, a novel 3-benzazepine alkaloid isolated from the freshwater blue-green alga Aphanizomenon flos-aquae, has been synthesized in the antipodal forms starting from (R)-0-benzylglycidol to establish the absolute configuration of the natural product as (IR, 4R). ... Aphanorphinel (1) , isolated from the freshwater blue-green alga Aphanizomenon flus-aquae, possesses an interesting 3-benzazepine framework closely related to the ...