Total synthesis of zaragozic acid A (squalestatin S1). Degradation to a relay compound and reassembly of the natural product

…, S Caron, CH Heathcock

文献索引：Stoermer, Doris; Caron, Stephane; Heathcock, Clayton H. Journal of Organic Chemistry, 1996 , vol. 61, # 26 p. 9115 - 9125

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被引用次数: 65

摘要

Zaragozic acid A (squalestatin S1)(1) was converted into the simpler derivative 2, which was reconverted into the natural product, thus establishing 2 as a viable relay compound for total synthesis of 1. The degradation (Scheme 1) consisted of formation of the tri-tert-butyl ester (3), from which the two side chains were sequentially removed to obtain 8. Aldehyde 8 was converted into dimethyl acetal 2 in standard fashion. The C6 acyl side chain 14 was ...