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Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (−)‐Elisabethadione
Author(s) -
O'Hora Paul S.,
IncertiPradillos Celia A.,
Kabeshov Mikhail A.,
Shipilovskikh Sergei A.,
Rubtsov Aleksandr E.,
Elsegood Mark R. J.,
Malkov Andrei V.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500176
Subject(s) - stereocenter , catalysis , lewis acids and bases , enantioselective synthesis , cationic polymerization , chemistry , base (topology) , combinatorial chemistry , diterpene , stereochemistry , organic chemistry , mathematics , mathematical analysis
A new, highly efficient Lewis base catalyst for a practical enantio‐ and diastereoselective crotylation of unsaturated aldehydes with E‐ and Z ‐crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (−)‐elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy‐Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.