Synthetic Studies on Cyclocitrinol: Construction of the ABC Ring System Based on Epoxy–Nitrile Cyclization

Autor:	Keiji Tanino, Kazuto Sato
Rok vydání:	2020
Předmět:	chemistry.chemical_compound Olefin fiber Nitrile chemistry Bicyclic molecule Stereochemistry Organic Chemistry Total synthesis Moiety Ring (chemistry) Enone Heptanone
Zdroj:	Synlett. 32:674-678
ISSN:	1437-2096 0936-5214
DOI:	10.1055/a-1334-6100
Popis:	The stereoselective synthesis of a model compound containing the ABC ring system of cyclocitrinol was accomplished. After connecting a C ring allyltitanium segment with an A ring bi­cyclo[4.1.0]heptanone segment, the seven-membered B ring moiety was constructed by an intramolecular cyclization reaction of an epoxy nitrile. The enone moiety was introduced through an oxidative decyanation reaction, and the bicyclo[4.4.1]undecane skeleton with the highly strained olefin moiety was formed through a ring-opening reaction of the bicyclo[4.1.0]heptane substructure.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6c3ebedc95a9ca699a664c918e83424a https://doi.org/10.1055/a-1334-6100 Zobrazit plný text záznamu