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Intramolecular Diels–Alder (IMDA) Studies toward the Synthesis of Australifungin. Stereocontrol in the Acetate Aldol Reaction of β,β′-Branched Aldehydes

Author:
Williams, David R., Klein, J. Cullen
Source:
Organic letters 2016 v.18 no.3 pp. 420-423
ISSN:
1523-7052
Subject:
acetates, aldehydes, chemical structure, cycloaddition reactions, nitroalkenes, optical isomerism, titanium
Abstract:
Studies of australifungin illustrate an enantiocontrolled synthesis of the trans-decalin core 28 via an intramolecular [4π + 2π] cycloaddition. This strategy utilizes the nitroalkene dienophile of 27 as a surrogate ketene equivalent. Stereocontrol at C-2 is critically important for an effective intramolecular Diels–Alder (IMDA) process. Our studies report high asymmetric induction using a nonracemic Duthaler titanium enolate in the acetate aldol reaction with β,β′-branched aldehyde 13 to introduce the required C-2 chirality.
Agid:
5792279