Application of the aza-Claisen rearrangement to the total synthesis of natural products: (-)-Isoiridomyrmecin

1 January 1994

journal article
Published by Walter de Gruyter GmbH in Pure and Applied Chemistry

Vol. 66 (10-11) , 2071-2074
https://doi.org/10.1351/pac199466102071

Abstract

Utilizing the aza-Claisen rearrangement recently developed by the authors, a straightforward synthesis of (-)-isoiridomyrmecin was achieved. A new reagent system, TMAD-Bu3P in benzene, was developed en route for the Mitsunobu type of the reactions. This system was found to be more effective to the nucleophiles of wider pKu range. The stable phosphoranes were also found to be effective in this type of reactions.

Keywords

AZA CLAISEN
CLAISEN REARRANGEMENT
ISOIRIDOMYRMECIN
STRAIGHTFORWARD
NUCLEOPHILES
BU3P

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