Tetrahedron Letters

Stereoselective formal total synthesis of the cyclodepsipeptide (−)-spongidepsin

S Chandrasekhar, SR Yaragorla, L Sreelakshmi

Index: Chandrasekhar, Srivari; Yaragorla, Srinivasa Rao; Sreelakshmi, Lella Tetrahedron Letters, 2007 , vol. 48, # 41 p. 7339 - 7342

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Citation Number: 13

Abstract

As outlined in our retrosynthetic analysis of 1 (Scheme 1), MacMillan α-hydroxylation of a (−)-citronellol derivative introduces the chirality 6 at C9, an Enders auxillary mediated enantioselective methylation at C4, Grubbs RCM to connect C5–C6 and Yamaguchi cyclization to build the macrocycle between C9 and C15 are the key steps. All these transformations were achieved with precision to build this scarce natural product. The key scaffolds viz. A, B, and C were prepared ...