Internal Nucleophilic Termination in Acid??Mediated Polyene Cyclisations: Synthetic access to methyle homologs of (±)??Ambrox® and its diastereoisomers

…, W Giersch, W Thommen, KH Schulte??Elte

Index: Snowden, Roger L.; Eichenberger, Jean-Claude; Giersch, Wolfgang; Thommen, Walter; Schulte-Elte, Karl H. Helvetica Chimica Acta, 1993 , vol. 76, # 4 p. 1608 - 1618

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Citation Number: 13

Abstract

Abstract Treatment of ten monocyclic dienols 8–11 with an excess of fluorosulfonic acid in 2- nitropropane at− 90 afforded diastereoisomeric mixtures of racemic tricyclic ethers 12–14 in 81–91% yield (see tables 1 and 2). These transformations represent further examples of biomimetic acid-mediated cyclisations in which an OH group serves as the internal nucleophilic terminator. A non-synchronous process is postulated, and the examples ...