First asymmetric total synthesis of Us-7 and -8, novel D-seco Corynanthe-type oxindole alkaloids from Uncaria attenuata: structure revision of Us-7 and determination of absolute stereochemistry

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

doi:10.1021/ol035128a

First asymmetric total synthesis of Us-7 and -8, novel D-seco Corynanthe-type oxindole alkaloids from Uncaria attenuata: structure revision of Us-7 and determination of absolute stereochemistry

Org Lett. 2003 Aug 7;5(16):2967-70. doi: 10.1021/ol035128a.

Authors

Hiromitsu Takayama¹, Rika Fujiwara, Yasuko Kasai, Mariko Kitajima, Norio Aimi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

PMID: 12889920
DOI: 10.1021/ol035128a

Abstract

[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.