Total Synthesis of (−)??Zampanolide and Structure–Activity Relationship Studies on (−)??Dactylolide Derivatives

…, L Betschart, J Schuster, J Gertsch…

Index: Zurwerra, Didier; Glaus, Florian; Betschart, Leo; Schuster, Julia; Gertsch, Juerg; Ganci, Walter; Altmann, Karl-Heinz Chemistry - A European Journal, 2012 , vol. 18, # 52 p. 16868 - 16883

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Citation Number: 17

Abstract

Abstract A new total synthesis of the marine macrolide (−)-zampanolide (1) and the structurally and stereochemically related non-natural levorotatory enantiomer of (+)- dactylolide (2), that is, ent-2, has been developed. The synthesis features a high-yielding, selective intramolecular Horner–Wadsworth–Emmons (HWE) reaction to close the 20- membered macrolactone ring of 1 and ent-2. The β-keto phosphonate/aldehyde precursor ...

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