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Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone α1 Using Lithiation/Borylation Reactions
Author(s) -
Pulis Alexander P.,
Fackler Philipp,
Aggarwal Varinder K.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400714
Subject(s) - stereoselectivity , borylation , diastereomer , chemistry , stereochemistry , mating type , alcohol , phytophthora , combinatorial chemistry , biology , botany , organic chemistry , alkyl , biochemistry , catalysis , gene , aryl
The universal mating hormone α 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28 % overall yield. Key CC bond‐forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91 %, the highest obtained to date.