Paul-Celia-Misha-3b.pdf (341.77 kB)
Download fileCatalytic asymmetric crotylation of aldehydes: application in total synthesis of (−)‐elisabethadione
journal contribution
posted on 2015-02-27, 15:07 authored by Paul O'Hora, Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Mark ElsegoodMark Elsegood, Andrei MalkovAndrei MalkovA 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 (À)-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.
Funding
We thank the Leverhulme Trust for the Research grant F00 261AD and LU for studentships to P.O.H. and C.A .I.P.
History
School
- Science
Department
- Chemistry