Synthesis of (±)-loliolide ((±)-digiprolactone)

Autor:	F. Sondheimer, J.N. Marx
Rok vydání:	1966
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Drug Discovery chemistry.chemical_element Organic chemistry Optically active Biochemistry Selenium Isophorone
Zdroj:	Tetrahedron. 22:1-7
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)82163-3
Popis:	(±)-Loliolide ((±)-digiprolactone) (I) has been synthesized from isophorone (IV) by two routes. The first utilized the oxidative lactonization of the mono-unsaturated acetoxy-ester XIb with selenium dioxide as a key step, while the second involved the cyclization of the doubly unsaturated keto-ester XVa to XVI with conc. sulphuric acid. The synthetic racemic compound proved to be identical with a sample prepared from natural optically active loliolide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b8e030d48fe716752034074181f6d1a1 https://doi.org/10.1016/s0040-4020(01)82163-3 Zobrazit plný text záznamu