Three-Step Synthesis of (±)-Preussin from Decanal

Autor:	Antonio C. B. Burtoloso, Rafael M. P. Dias, Vagner D. Pinho, Isac G. Rosset
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Aldehydes Molecular Structure Chemistry Stereochemistry Organic Chemistry Stereoisomerism Decanal chemistry.chemical_compound SÍNTESE ORGÂNICA Ylide Organic chemistry Stereoselectivity Anisomycin
Zdroj:	Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo5011558
Popis:	A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an α,β-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::31605c948d6d8d4bf7bd7463b35d9546 https://doi.org/10.1021/jo5011558 Zobrazit plný text záznamu