Total Synthesis of (±)-Silphinene: non photochemical cyclobutenic route to a crucial intermediate

Autor:	Michel Miesch, Michel Franck-Neumann, Laurence Miesch-Gross
Rok vydání:	1997
Předmět:	Allylic rearrangement Bicyclic molecule Organic Chemistry Total synthesis Ether Alcohol Silyl enol ether Cyclopentanone Biochemistry Medicinal chemistry Cycloaddition chemistry.chemical_compound chemistry Drug Discovery
Zdroj:	Tetrahedron. 53:2103-2110
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(96)01159-3
Popis:	The cyclobutenic ester 1, readily available by thermal [2+2] cycloaddition of the silyl enol ether derived from cyclopentanone with ethyl propynoate, is easily transformed into the diquinanic alcohol 3 via the bicyclo [2.1.0] pentane intermediate 2. After protection as the thexyldimethylsilyl ether, an allylic oxidation stereospecifically introduces a hydroxyl group at position 8. Following formation of the benzyl ether, the diquinane 9 was then transformed in four steps into the triquinane 20 using a silyl-assisted Nazarov type cyclisation. From this intermediate, (±)-silphinene has previously been synthesized.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0dbb61e65089d8e203610cb4979cb355 https://doi.org/10.1016/s0040-4020(96)01159-3 Zobrazit plný text záznamu Full Text from ScienceDirect