Skip navigation
Skip navigation

Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids

Lan, Ping; Banwell, Martin; Willis, Anthony


The thermally induced electrocyclic ring-opening of C2-symmetric (meso) 6,6-dibromobicyclo[3.1.0]hexanes such as 10 in the presence of the chiral, nonracemic 1°-amine 28 afforded a ca. 1:1 mixture of the diastereoisomeric and chromatographically separable 1-amino-2-bromo-2-cyclohexenes 37 (42%) and 38 (45%). Each of these was elaborated over 13 steps, including Suzuki–Miyaura cross-coupling, radical cyclization, and Pictet–Spengler reactions, into (−)- or (+)-crinane (1 or ent-1, respectively)....[Show more]

CollectionsANU Research Publications
Date published: 2019-02-06
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.9b00018
Access Rights: Open Access


File Description SizeFormat Image
Application of Electrocyclic Ring-opening and Desymmetrizing.pdf994.3 kBAdobe PDFThumbnail

Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  19 May 2020/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator