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Highly Diastereoselective, Tandem, Three-Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β-Lactone Intermediates

Authors


  • We thank the NIH (GM 069784) and the Welch Foundation (A-1280) for funding this work. We thank Kay Morris and Dr. Ziad Moussa, as well as Profs. Dan Singleton and Brian Connell for helpful discussions.

Abstract

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Like falling dominoes! A novel tandem, three-component reaction is described that generates up to two C[BOND]C bonds, one C[BOND]O bond, and three additional stereocenters leading to substituted tetrahydrofuran units. This process involves a tandem Mukaiyama aldol-lactonization/reductive cyclization and proceeds via a silylated β-lactone intermediate. The method was applied to prepare the tetrahydrofuran fragment of colopsinol B. Py=2-pyridyl.

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