Synthesis of the C29-C44 Portion of Spongistatin 1 (Altohyrtin A)

…, RW Scott, CH Heathcock

Index: Wallace, Grier A.; Scott, Robert W.; Heathcock, Clayton H. Journal of Organic Chemistry, 2000 , vol. 65, # 13 p. 4145 - 4152

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Citation Number: 58

Abstract

Two synthetic approaches to the C29-C44 portion of spongistatin 1 (altohyritin A) have been developed. The key step of the first approach relies on the Claisen rearrangement of glucal 18 to provide ester 20a. This intermediate was advanced to silyl enol ether 30, which was coupled under Mukaiyama aldol conditions with aldehyde 3. Cyclization of this aldol adduct completed our first synthesis of the C29-C44 portion of spongistatin 1, requiring 25 total ...

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