Synthesis of four possible stereoisomers of 1, 2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid,(±)-erythratidine 1

S Hosoi, M Nagao, Y Tsuda, K Isobe, T Sano…

Index: Hosoi, Shinzo; Nagao, Motoyoshi; Tsuda, Yoshisuke; Isobe, Kimiaki; Sano, Takehiro; Ohta, Tomihisa Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 10 p. 1505 - 1511

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Citation Number: 19

Abstract

Erythrinan alkaloids possessing an aromatic D-ring are classified into two sub-groups, dienoid and alkenoid types, according to the structure of the A/B-rings. 2 More than thirty members of the latter alkaloid type are now known. Most of them bear an additional chiral center at C-2 (for example, erythratidine 1), 3 whose stereochemistry has been elucidated principally based on the coupling constant between H-2 and H-3 in the 1 H NMR spectrum. 3b Although total ...