Total Synthesis of (−)-Blepharocalyxin D and Analogues

Autor:	Adam J. Bunt, Christopher D. Bailey, Christine L. Willis, Benjamin D. Cons
Rok vydání:	2013
Předmět:	Molecular Structure Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Blepharocalyxin D Total synthesis Stereoisomerism Alpinia blepharocalyx Prins reaction Biochemistry Stereocenter Lactones Alcohols Alpinia Physical and Theoretical Chemistry Diarylheptanoids Pyrans
Zdroj:	Organic Letters. 15:2046-2049
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol400736w
Popis:	An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with γ,δ-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5e9989494902767db4478dbdd4cffc16 https://doi.org/10.1021/ol400736w Zobrazit plný text záznamu