Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone

Autor:	Scott V. Plummer, Samarjit Patnaik, David R. Williams
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Organic Chemistry Diol Biochemistry Aldehyde Asymmetric induction Chemical synthesis Article chemistry.chemical_compound Electrophilic substitution chemistry Drug Discovery Organic chemistry Stereoselectivity Chemoselectivity Lactone
Zdroj:	Tetrahedron. 67:5083-5097
ISSN:	0040-4020
DOI:	10.1016/j.tet.2011.05.020
Popis:	Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in SE′ reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at −78 °C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of SE′ reactions leading to the C1–C9 aldehyde 14, and the bis-tetrahydropyran 59, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8e89c1943447aedb37b07a197edf0d71 https://doi.org/10.1016/j.tet.2011.05.020 Zobrazit plný text záznamu Full Text from ScienceDirect