Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation

Comméiras, Laurent, Moses, John E., Adlington, Robert M., Baldwin, Jack E., Cowley, Andrew R., Baker, Christopher M., Albrecht, Birgit, Grant, Guy H. (October 2006) Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation. Tetrahedron, 62 (42). pp. 9892-9901. ISSN 0040-4020

URL: http://www.sciencedirect.com/science/article/pii/S...

DOI: 10.1016/j.tet.2006.08.010

Abstract

An asymmetric total synthesis of the novel and structurally complex epoxyquinol natural product (+)-panepophenanthrin has been accomplished, in which a biomimetic Diels–Alder dimerisation is a key step. The key monomeric precursor was assembled by an efficient Stille cross coupling of two readily available building blocks that upon standing underwent a diastereospecific dimerisation cascade in excellent yield.

Item Type:	Paper
Uncontrolled Keywords:	Total synthesis Biomimetic synthesis Stille coupling Dimerisation cascade Epoxyquinol Ubiquitin activating enzyme E1
CSHL Authors:	Moses, John E.
Depositing User:	Matthew Dunn
Date:	16 October 2006
Date Deposited:	17 Nov 2020 21:32
Last Modified:	17 Nov 2020 21:32
URI:	https://repository.cshl.edu/id/eprint/39792

Actions (login required)

Administrator's edit/view item