Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis

BM Trost, PE Harrington, JD Chisholm…

Index: Trost, Barry M.; Wrobleski, Stephen T.; Chisholm, John D.; Harrington, Paul E.; Jung, Michael Journal of the American Chemical Society, 2005 , vol. 127, # 39 p. 13589 - 13597

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Citation Number: 40

Abstract

The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene-alkyne coupling to forge the C15-C16 bond. Using the reported structure 1 as a starting point, a number of diastereomers of amphidinolide A were prepared. Deviations of ...