ChemInform Abstract: Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols

Autor:	Geoffrey W. Coates, Yanping Wang, George A. O'Doherty, Brandon J. Tiegs, Michael Mulzer
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Chemistry Yield (chemistry) Functional group Enantioselective synthesis Organic chemistry Total synthesis Regioselectivity General Medicine Lewis acids and bases Carbonylation Catalysis
Zdroj:	ChemInform. 46
ISSN:	0931-7597
DOI:	10.1002/chin.201510283
Popis:	A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)4](-) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-β-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8348aac02a5d5afc6eec30c2a22dc960 https://doi.org/10.1002/chin.201510283 Zobrazit plný text záznamu Plný text