Stereoselective approach to potential scaffold of A-nor B-aromatic OSW-1 analogues via [4+2] cycloaddition of o-quinodimethane

Autor:	Bozhi Li, Daishiro Minato, Seiji Masuda, Hideo Nemoto, Dejun Zhou, Kenji Sugimoto, Yuji Matsuya
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Addition reaction Aglycone chemistry Benzocyclobutene Stereochemistry Organic Chemistry Drug Discovery Diol Substrate (chemistry) Stereoselectivity Biochemistry Cycloaddition
Zdroj:	Tetrahedron. 70:3981-3987
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.04.079
Popis:	A-nor B-aromatic steroidal skeleton was efficiently constructed by means of o -quinodimethane chemistry with exclusive stereoselectivity. The benzocyclobutene substrate for generation of the o -quinodimethane intermediate and subsequent [4+2] cycloaddition could be synthesized via ( E )-selective Julia–Kocienski olefination and diastereoselective Grignard addition reactions. The synthesized tricyclic steroid-like compound with a trans -diol substructure would be utilized for divergent syntheses of potentially antitumor OSW-1 analogues with the truncated steroidal aglycone.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8225b9373746f323e661d804070b01f8 https://doi.org/10.1016/j.tet.2014.04.079 Zobrazit plný text záznamu Full Text from ScienceDirect