Diels–Alder Reactions of γ-Hydroxybutenolides: Approach to the Himbacine Tricyclic Core

Autor:	Jason S. George, Natalie E. Jasiewicz, Daniel Beideman, Dasan M. Thamattoor, Stephanie M. Petersen, Samantha M. Zeiders, Ryan E. Cerbone, William H. Miles, Ida B. G. Suarsana, Joseph V. Leo, Nicholas J. Albano, Barbara J. Naimoli
Rok vydání:	2016
Předmět:	010405 organic chemistry Stereochemistry Organic Chemistry Regioselectivity Alkylation 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Lewis acid catalysis Stereocenter chemistry.chemical_compound chemistry Himbacine Lewis acids and bases Diels–Alder reaction
Zdroj:	Synthesis. 48:924-934
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0035-1561348
Popis:	The Diels–Alder reaction of γ-hydroxybutenolides with dienes gave good yields of cycloadducts under thermal and Lewis acid catalyzed conditions. The application of this methodology to a more complex system was demonstrated by the synthesis of a model system for the tricyclic himbacine core. The stereo- and regioselective Diels–Alder reaction established three of the stereogenic centers, with the fourth stereogenic center secured by diastereoselective alkylation of the cycloadduct.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7b5add0e182ecf966317e6194f4e263f https://doi.org/10.1055/s-0035-1561348 Zobrazit plný text záznamu