Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Autor:	Thunwadee Ritthiwigrom, Andrew S. Davis, Stephen G. Pyne, Arife Yazici, Christopher W. G. Au, Ian Rhys Morgan
Rok vydání:	2008
Předmět:	Stemona biology General Chemical Engineering Alkaloid Alkaloid synthesis Iminium Indolizidine General Chemistry biology.organism_classification chemistry.chemical_compound chemistry Pyrrolizidine Organic chemistry QD Azepine Mannich reaction
Zdroj:	Pure and Applied Chemistry. 80:751-762
ISSN:	1365-3075 0033-4545
DOI:	10.1351/pac200880040751
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::43d4d4a03fd79862852e03cd9ac9ae9f https://doi.org/10.1351/pac200880040751 Zobrazit plný text záznamu