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Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (−)‐elisabethadione

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journal contribution
posted on 27.02.2015, 15:07 by Paul O'Hora, Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Mark ElsegoodMark Elsegood, Andrei MalkovAndrei Malkov
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 (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

Published in

Chemistry - A European Journal

Volume

21

Issue

12

Pages

4551 - 4555

Citation

O'HORA, P. ... et al, 2015. Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (- )-elisabethadione. Chemistry - A European Journal, 21(12), pp.4551-4555.

Publisher

© Wiley-VCH Verlag GmbH &Co

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2015-02-06

Notes

This is the peer reviewed version of the following article: O'HORA, P. ... et al, 2015. Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (- )-elisabethadione. Chemistry - A European Journal, 21(12), pp.4551-4555, which has been published in final form at http://dx.doi.org/10.1002/chem.201500176. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

ISSN

0947-6539

eISSN

1521-3765

Language

en