A modular approach to marine macrolide construction. 3. Enantioselective synthesis of the C1-C28 sector of spongistatin 1 (altohyrtin A).
[structure: see text] A completely stereocontrolled approach to assembly of the major C1-C28 subunit of spongistatin 1 (altohyrtin A) is described. Key steps included the control of two asymmetric aldols by means of Fujita-Nagao (chiral N-acyl-1,3-thiazolidine-2-thione auxiliary) and Mukaiyama (BF3 x OEt2-promoted enolsilane coupling) protocols in complex settings.
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Evans Chemical Laboratories, The Ohio State University, Columbus 43210, USA.
Paquette
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D000818:Animals; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D011161:Porifera; D013237:Stereoisomerism; D000095702:Polyether Toxins
D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins