Premium
Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
Author(s) -
Melikhova Ekaterina Y.,
Pullin Robert D. C.,
Winter Christian,
Donohoe Timothy J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604764
Subject(s) - epimer , negishi coupling , chemistry , total synthesis , stereochemistry , molecule , combinatorial chemistry , organic chemistry , catalysis
The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO 2 H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolidinone stereochemistry of both compounds was confirmed by synthesizing epimers of the proposed structures. The spectroscopic data of these epimers were in complete agreement with those for the naturally derived material.