Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules

被引：17

作者：

Sunden, Henrik ^{[1
]}

Olsson, Roger ^{[1
,2
]}

机构：

[1] Univ Gothenburg, Dept Chem Med Chem, SE-41296 Gothenburg, Sweden

[2] ACADIA Pharmaceut AB, S-20512 Malmo, Sweden

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 21期

关键词：

ENANTIOSELECTIVE SYNTHESIS; MITSUNOBU REACTION; ALPHA-IODINATION; MORPHINE; TRYPANOTHIONE; ALKALOIDS;

D O I：

10.1039/c0ob00331j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.

引用

页码：4831 / 4833

页数：3