ChemInform Abstract: A Novel One-Step Diastereo- and Enantioselective Formation of trans-Azetidinones and Its Application to the Total Synthesis of Cholesterol Absorption Inhibitors

Autor:	YeeShing Wong, Zhixian Ding, Guang-Zhong Wu, Xing Chen
Rok vydání:	2010
Předmět:	Chemistry polycyclic compounds Enantioselective synthesis Side chain Total synthesis Aldol condensation One-Step General Medicine Combinatorial chemistry Cholesterol absorption
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199936126
Popis:	An efficient and practical asymmetric process was developed for the synthesis of azetidinone-based cholesterol absorption inhibitors. Key to this synthesis was the discovery of a novel one-step diastereo- and enantioselective formation of trans β-lactams starting from commercially available 3(S)-hydroxy-γ-lactone. Various trans β-lactams can be prepared in good yields and with better than 95:5 enantio- and diastereoselctivity. A Lewis acid-catalyzed aldol condensation and a highly enantioselective oxazaborolidine-catalyzed chiral reduction completes the side chain.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e321d8217160a20fabbfe0f038028d0e https://doi.org/10.1002/chin.199936126 Zobrazit plný text záznamu Plný text