Internal nucleophilic termination in biomimetic acid mediated polyene cyclizations: stereochemical and mechanistic implications. Synthesis of (.+-.)-Ambrox and its …

…, P Sonnay, C Vial, KH Schulte-Elte

Index: Snowden, Roger L.; Eichenberger, Jean-Claude; Linder, Simon M.; Sonnay, Philippe; Vial, Christian; Schulte-Elte, Karl H. Journal of Organic Chemistry, 1992 , vol. 57, # 3 p. 955 - 960

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Citation Number: 55

Abstract

Treatment of 10 shcturally related trienols and dienols 5-8 with an exce88 of fluoro~ ulfonic acid in 2-nitropropane at-90" C afforded, in 74-87% yield, diastereoisomeric mixtures of the odoriferous norlabdane oxides 9-15 ((-)-9 (Ambrox) is a naturally occurring ambergris odorant). These transformations represent examples of efficient biomimetic acid-mediated cyclizations in which the hydroxyl group servea as the internal nucleophilic terminator. ...

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