Total synthesis of optically active monocrotaline, a carcinogenic pyrrolizidine alkaloid possessing an eleven-membered retronecine dilactone

H Niwa, T Ogawa, O Okamoto, K Yamada

Index: Niwa, Haruki; Ogawa, Takeshi; Okamoto, Osamu; Yamada, Kiyoyuki Tetrahedron, 1992 ,  vol. 48,  # 48  p. 10531 - 10548

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Citation Number: 33

Abstract

A total synthesis of the natural enantiomer of monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids having an 11-membered retronecine dilactone was achieved through regioselective coupling of (+)-retronecine (3) and the optically active protected necic acid 8, the latter being prepared enantioselectively from the meso-diester 11.