Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy

…, S Nakamura, N Watanabe, O Kataoka…

Index: Hirata, Yuuki; Nakamura, Seiichi; Watanabe, Nobuhide; Kataoka, Osamu; Kurosaki, Takahiro; Anada, Masahiro; Kitagaki, Shinji; Shiro, Motoo; Hashimoto, Shunichi Chemistry - A European Journal, 2006 , vol. 12, # 35 p. 8898 - 8925

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Citation Number: 41

Abstract

Abstract A carbonyl ylide cycloaddition approach to the squalene synthase inhibitors zaragozic acids A and C is described. The carbonyl ylide precursor 8 was synthesized starting from di-tert-butyl D-tartrate (47) via an eleven-step sequence involving the regioselective reduction of the mono-MPM (MPM= 4-methoxybenzyl) ether 48 with LiBH 4 and the diastereoselective addition of sodium tert-butyl diazoacetate to α-keto ester 10. ...