Journal of the American Chemical Society

A simplified total synthesis of cytochalasins via an intramolecular Diels-Alder reaction

G Stork, E Nakamura

Index: Stork, Gilbert; Nakamura, Eiichi Journal of the American Chemical Society, 1983 , vol. 105, # 16 p. 5510 - 5512

Full Text: HTML

Citation Number: 97

Abstract

5 7, R,= TPH; R,= Cbz 8, R,= H, R,= AC 9, R,= R,= Ac (63-73%), phosphonate 66 to give the unsaturated lactam 7, which was then transformed to the N-acetylhydroxypyrrolone 8 (70% yield from 5) by appropriate exchange of protective groups. The optical purity of 8 (80% ee from'H NMR of its MTPA ester) was confirmed by the rotation of its diacetate 9:[a] 21+ 90.9'(c 3.23). Ia