Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Pyne, Stephen G., Au, Christopher W. G., Davis, Andrew S., Morgan, Ian Rhys ORCID: https://orcid.org/0000-0002-0253-1855, Ritthiwigrom, Thunwadee and Yazici, Arife 2008. Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis. Pure and Applied Chemistry 80 (4) , pp. 751-762. 10.1351/pac200880040751

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Abstract

We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids and using the borono-Mannich reaction on cyclic N-acyliminium ions, are encouraging, as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	alkaloids; amino alcohols; boronic acids; Mannich reaction; Stemona
Additional Information:	21st International Congress for Heterocyclic Chemistry (ICHC 21), Sydney, Australia, 15–20 July 2007. Pdf uploaded in accordance with publisher's policy at http://www.sherpa.ac.uk/romeo/issn/0033-4545/ (accessed 26/02/2014).
Publisher:	International Union of Pure and Applied Chemistry
ISSN:	00334545
Date of First Compliant Deposit:	30 March 2016
Last Modified:	04 May 2023 22:55
URI:	https://orca.cardiff.ac.uk/id/eprint/48279

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