Bis-heteroannulation. 16. A synthetic approach to geigerin

Autor:	Peter A. Jacobi, Kim M. Touchette, Harold G. Selnick
Rok vydání:	1992
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Annulation Ketone chemistry Hydride Organic Chemistry Organic chemistry Ether Alcohol Chemoselectivity Selectivity Oxazole
Zdroj:	The Journal of Organic Chemistry. 57:6305-6313
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00049a044
Popis:	Furano alcohol 5, the key intermediate in our proposed synthesis of the guaianolide sesquiterpene geigerin (1), was prepared by a novel sequence of reactions which includes a chemoselective oxy-Cope transformation of enynols of general structure 42. Although 42 itself underwent oxy-Cope reaction with exclusive triple-bond participation, the corresponding tert-butyldimethylsilyl ether 46 gave the desired vinyl silyloxy Cope product 48 with 100% selectivity. The conversion of acetylenic oxazole 48 to 5 was then effected by a highly efficient (Diels-Alder)-(retro-Diels-Alder) transformation to generate the guaiane ketone 20, followed by hydride reduction
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c8f1b42b3b8b27acb2755ae233b1bd00 https://doi.org/10.1021/jo00049a044 Zobrazit plný text záznamu