Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A

被引：15

作者：

Nagumo, S ^{[1
]}

Nishida, A ^{[1
]}

Yamazaki, C ^{[1
]}

Matoba, A ^{[1
]}

Murashige, K ^{[1
]}

Kawahara, N ^{[1
]}

机构：

[1] Hokkaido Coll Pharm, Otaru, Hokkaido 0470264, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 24期

关键词：

TAN1251A; antimuscarinic activity; aldol reaction; Curtius rearrangement;

D O I：

10.1016/S0040-4020(02)00436-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-TAN1251A possessing an antimuscarinic activity was achieved. Carboxylic acid (1) was converted into carbamate (3) through a sequence of alkylation and Curtius rearrangement. After a few functional group interconversions of 3, the corresponding amine (9) was converted into an azaspiro molecule (18) through cyclization and installation of a C-2 unit. Hydrolysis of 18 followed by lactam formation afforded tricyclic compound (20). Coupling of 20 with aldehyde (22) gave two epimeric adducts, (23A) and (23B), which were converted into TAN1251A by four steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4917 / 4924

页数：8

共 13 条

[1] RULES FOR RING-CLOSURE [J].