Synthesis of the C1-C28 Portion of Spongistatin 1 (Altohyrtin A)

…, CJ Hayes, CH Heathcock

Index: Claffey, Michelle M.; Hayes, Christopher J.; Heathcock, Clayton H. Journal of Organic Chemistry, 1999 , vol. 64, # 22 p. 8267 - 8274

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Citation Number: 51

Abstract

A synthetic approach was developed to the C1-C28 subunit of spongistatin 1 (altohyrtin A, 65). The key step was the coupling of the AB and CD spiroketal moieties via an anti-aldol reaction of aldehyde 62 and ethyl ketone 57. The development of a method for the construction of the AB spiroketal fragment is described and included the desymmetrization of C 2-symmetric diketone 10 and the differentiation of the two primary alcohols of 16. ...