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

被引：7
|
作者：
Li, Bozhi [1 ]
Masuda, Seiji [1 ]
Minato, Daishiro [1 ]
Zhou, Dejun [2 ]
Sugimoto, Kenji [1 ]
Nemoto, Hideo [3 ]
Matsuya, Yuji [1 ]
机构：
[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Toyama 9300194, Japan
[2] Henan Polytech Univ, Sch Phys & Chem, Jiaozou 454000, Peoples R China
[3] Lead Chem Co Ltd, Toyama 9300912, Japan
来源：
TETRAHEDRON | 2014年 / 70卷 / 26期
关键词：
o-Quinodimethane; Julia-Kocienski olefination; OSW-1; Steroidal skeleton; DIHYDROFURAN-FUSED PERHYDROPHENANTHRENES; CHOLESTANE GLYCOSIDES; NEUROSTEROID ANALOGS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; CONDENSATION; OLEFINATION;
D O I：
10.1016/j.tet.2014.04.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2014 Elsevier Ltd. All rights reserved.
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页码：3981 / 3987
页数：7
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