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Letter

Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

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Michael T. Crimmins* and Matthew W. Haley

Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599

Org. Lett., 2006, 8 (19), pp 4223–4225

DOI: 10.1021/ol061339e

Publication Date (Web): August 18, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, crimmins@email.unc.edu

Abstract

Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.

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Published In Issue September 14, 2006
Received June 1, 2006

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Letter

Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

Abstract

Available Supporting Information for This Article

PDF

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History

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Related Content

(+)-Sorangicin A Synthetic Studies. Construction of the C(1−15) and C(16−29) Subtargets

An Efficient, Second-Generation Synthesis of the Signature Dioxabicyclo[3.2.1]octane Core of (+)-Sorangicin A and Elaboration of the (Z,Z,E)-Triene Acid System

Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

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