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
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Lan, Ping; Banwell, Martin; Willis, Anthony
Description
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]
Collections | ANU Research Publications |
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Date published: | 2019-02-06 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/196689 |
Source: | Journal of Organic Chemistry |
DOI: | 10.1021/acs.joc.9b00018 |
Access Rights: | Open Access |
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Application of Electrocyclic Ring-opening and Desymmetrizing.pdf | 994.3 kB | Adobe PDF |
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