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Synthesis of Amathaspiramides by Aminocyanation of Enoates
Author(s) -
O'Connor Matthew,
Sun Chunrui,
Lee Daesung
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503982
Subject(s) - diazomethane , cycloaddition , chemistry , trimethylsilyl , formal synthesis , lithium (medication) , bond cleavage , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , medicine , endocrinology
Concise routes for the total and formal syntheses of the amathaspiramides were developed through a formal [3+2] cycloaddition between lithium(trimethylsilyl)diazomethane and α,β‐unsaturated esters. The effectiveness of this new cycloaddition for the construction of Δ 2 ‐pyrazolines containing a α‐ tert ‐alkylamino carbon center and subsequent facile protonolytic NN bond cleavage allows the synthesis of a key intermediate of the amathaspiramides and other α,α‐disubstituted amino acid derivatives.