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First Asymmetric Total Synthesis of Us-7 and -8, Novel D - s eco Corynanthe-Type Oxindole Alkaloids from Uncaria a ttenuata : Structure Revision of Us-7 and Determination of Absolute Stereochemistry

2003; American Chemical Society; Volume: 5; Issue: 16 Linguagem: Inglês

10.1021/ol035128a

1523-7060

Hiromitsu Takayama, Rika Fujiwara, Yasuko Kasai, Mariko Kitajima, Norio Aimi,

Traditional and Medicinal Uses of Annonaceae

[reaction: see text] Starting from (S)-glycidol, the asymmetric total synthesis of novel D-seco Corynanthe-type oxindoles Us-7 and Us-8 was accomplished. The structure of Us-7 was revised from the reported structure 1 with the (3R,7S) form to structure 22 with (3S,7R), and the absolute stereochemistry at C15 of both alkaloids was established.