Tetrahedron p. 3135 - 3142 (1990)
Update date:2022-08-02
Topics:
Huang, Dai-Fei
Huang, Liang
Asymmetric synthesis of (-)-dehydroclausenamide 1 by scheme 2 was reported. Sharpless epoxidation was applied to cinnamyl alcohol for introduction of two desired chiral centers and the potential hydroxyl group. The key intermediate, γ-lactam (-)-5, was obtained by regio-selective intramolecular cyclization of (-)-6. Subsequent stereo-selective reduction was achieved by reducing C3-tetrahydropyranyl ether of (-)-5. The title natural product was then obtained by successive tosylation, hydrolysis and cyclization.
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Doi:10.1055/s-0030-1259535
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