ネオオキサゾロマイシンの全合成

概要

論文の詳細を見る
The first enantioselective total synthesis of neooxazolomycin (1), structurally unique antitumor agent isolated from streptomyces sp., is described. The key steps of the synthesis involve the following newly developed synthetic methods : i) the novel dianion cyclocondensation reaction of amide-malonate 3 with ester 36 followed by stereoselective lactonization to give the fused bicyclic lactam-lactone terminus, ii) the four carbon homologation of aldehyde 41 to E, E-dienamide 45 via vinyliodide 43 by means of the mild Pd-catalyzed coupling with the vinylstannane 13, (iii) the diastereoselective Reformatsky type aldol reaction of Z-enal 48 with the tin (II) enolate derived from chiral oxazolidinone 15 to give R, S-oxazinedione 51. Utilizing the above key reactions and further manipulations afforded the right half amine 71 and the left half acid 68 in proper chiral form. Finally, the amide formation of them followed by deprotection gave the synthetic neooxazolomycin (1).
社団法人有機合成化学協会の論文