A tandem cycloaddition-ene strategy for the synthesis of (.+-.)-verrucarol and (.+-.)-4, 11-diepi-12, 13-deoxyverrucarol

BM Trost, PG McDougal, KJ Haller

Index: Trost; McDougal; Haller Journal of the American Chemical Society, 1984 , vol. 106, # 2 p. 383 - 395

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Citation Number: 28

Abstract

Abstract: A ring expansion of a 6, 5 to 6, 6 system provides a stereo-controlled entry into the polyhydrochromanones. The steric and electronic requirements of such a process are probed. For the synthesis of verrucarol, such a process involves the synthesis of a norapotrichothecene followed by the rearrangement to the trichothecane skeleton-a process that may be reminiscent of the biogenesis of trichothecanes. The reaction of l-( ...