Total Synthesis of Phorboxazole A

Authors


  • Generous financial support for this research was provided by the NIH (GM-41560). We acknowledge Prof. Craig J. Forsyth for providing us with detailed conditions for reproducing HRMS data for phorboxazole A and 1H NMR spectra of natural and synthetic material. We also thank Prof. Amos B. Smith for 1H NMR spectra of synthetic phorboxazole A for our comparison.

Abstract

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Asymmetric allylation reactions of stannyl-derived allyldiazaborolanes, a stereoselective cationic cyclization reaction for the formation of the fully substituted C22–C26 tetrahydropyran, and the use of a Julia olefination for the incorporation of the sensitive C37–C46 dienyl system are key features of a highly convergent, stereocontrolled total synthesis of phorboxazole A (see structure).

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