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Total Syntheses of Dalesconol A and B

Authors


  • We thank the NSF (CHE-0619638) for an X-ray diffractometer and Prof. Gerard Parkin, Wesley Sattler, and Aaron Sattler for performing all of the crystallographic analyses. We also thank Dr. George Sukenick for NMR assistance. Financial support was provided by Columbia University, the National Institutes of Health (R01M84994), the NSF (Predoctoral Fellowships to T.C.S. and A.G.R.), Eli Lilly (Grantee award to S.A.S), the Camille and Henry Dreyfus Foundation (New Faculty Award to S.A.S.), and the Research Corporation for Science Advancement (Cottrell Scholar Award to S.A.S.).

Abstract

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A polycyclic collapse: Use of a carefully designed acyclic intermediate participated in a cascade reaction that formed the entire core of the polyketide-derived dalesconols in a single flask (see scheme). A number of additional and carefully controlled synthetic operations completed an expeditious synthesis of both of these highly bioactive natural products as well as structural congenors.

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