Synthesis of macrocyclic trichothecanoids. Baccharin B5 and roridin E

…, C Gennari, JA Noguez, DA Pearson

Index: Still, W. Clark; Gennari, Cesare; Noguez, Jose A.; Pearson, Daniel A. Journal of the American Chemical Society, 1984 , vol. 106, p. 260 - 262

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Citation Number: 27

Abstract

The achiral Cl'-C5'segment was prepared from the t-BuMe2Si ether of 3-butyn-1-01 by ethoxycarboxylation (a, n-BuLi; b, ClCOOEt), conjugate methylation (Me2CuLi, Et20), 5 and reduction (LiAlH4) in 45% overall yield. Conversion to the chloride (NCS, Me2S) 6 and coupling with the sodium salt of 3 (THFHMPA, catalyst Bu, NI) was followed by desilylation (Bu4NF, THF) and Jones oxidation to give the required acid 4 (70-75% overall).