Tetrahedron

Synthesis of secoisoquinoline alkaloids: Total synthesis of cryptopleurospermine

MD Rozwadowska, M Chrzanowska

Index: Rozwadowska, Maria D.; Chrzanowska, Maria Tetrahedron, 1986 , vol. 42, # 24 p. 6669 - 6672

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Citation Number: 5

Abstract

Cryptopleurospermine (1), a 1, 2-secobenzylisoquinoline alkaloid was synthesized from hydrastinine derivative 2 and isovanillin 1, 3-propylene dithioacetal 3. The formation of CC bond between these two synthons involved addition of dilithio salt of dithian 3 to aldehyde group in 2. Reduction and hydrolysis of the masking group in addition product 4 furnished the synthesis.