Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C
…, Y Kawada, T Oishi, S Tanaka, Y Ogasawara, S Sasaki…
Index: Kobayashi, Shoji; Takahashi, Yusuke; Komano, Kazuo; Alizadeh, Babak H.; Kawada, Yuuya; Oishi, Tohru; Tanaka, Shin-Ichiro; Ogasawara, Yoshihiro; Sasaki, Shin-Ya; Hirama, Masahiro Tetrahedron, 2004 , vol. 60, # 38 p. 8375 - 8396
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Citation Number: 32
Abstract
The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary- based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left ...