Total synthesis of the furaquinocins

T Saito, T Suzuki, M Morimoto, C Akiyama…

Index: Saito, Takeshi; Suzuki, Takao; Morimoto, Munetsugu; Akiyama, Chikako; Ochiai, Takashi; Takeuchi, Kazuhiro; Matsumoto, Takashi; Suzuki, Keisuke Journal of the American Chemical Society, 1998 , vol. 120, # 45 p. 11633 - 11644

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Citation Number: 56

Abstract

A viable synthetic route to the furaquinocin-class antibiotics is described. The key steps include (1) Co-complex mediated stereospecific 1, 2-shift of an alkynyl group (9→ 6) to establish the C (2)-C (3) stereochemical relationship,(2) efficient construction of furanonaphthalene 20 from the sodium carboxylate derived from ester 19, and (3) stereoselective methylene transfer reaction to aldehyde 21 to establish the three ...