Synthesis of (-)-TAN1251A using 4-hydroxy-L-proline as a chiral source

被引：23

作者：

Nagumo, S ^{[1
]}

Matoba, A ^{[1
]}

Ishii, Y ^{[1
]}

Yamaguchi, S ^{[1
]}

Akutsu, N ^{[1
]}

Nishijima, H ^{[1
]}

Nishida, A ^{[1
]}

Kawahara, N ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2002年 / 58卷 / 49期

关键词：

(-)-TAN1251A; anti-muscarinic activity; synthesis 1-azaspiro[4.5]decane; trans-4-hydroxy-L-proline;

D O I：

10.1016/S0040-4020(02)01292-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic route of (-)-TAN1251A possessing an antimuscarinic activity was developed on the basis of alkylation of a trans-4-hydroxy-L-proline derivative and the subsequent construction of an azaspiro ring as key steps. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：9871 / 9877

页数：7

共 50 条

[1] Total synthesis of (±)-TAN1251A
Nagumo, S
Nishida, A
Yamazaki, C
Murashige, K
Kawahara, N
TETRAHEDRON LETTERS, 1998, 39 (25) : 4493 - 4496
[2] Facile synthesis of enantiopure (-)-TAN1251A
Mizutani, H
Takayama, J
Soeda, Y
Honda, T
TETRAHEDRON LETTERS, 2002, 43 (13) : 2411 - 2414
[3] An enantioselective formal total synthesis of (-)-TAN1251A
Auty, JMA
Churcher, I
Hayes, CJ
SYNLETT, 2004, (08) : 1443 - 1445
[4] Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A
Nagumo, S
Nishida, A
Yamazaki, C
Matoba, A
Murashige, K
Kawahara, N
TETRAHEDRON, 2002, 58 (24) : 4917 - 4924
[5] Stereoselective synthesis of dihydropyrimidinethione podand in the presence of l-proline or 4-hydroxy-l-proline and metal nitrates
E. S. Filatova
O. V. Fedorova
I. G. Ovchinnikova
K. A. Chistyakov
G. L. Rusinov
V. N. Charushin
Russian Chemical Bulletin, 2022, 71 : 1506 - 1513
[6] Stereoselective synthesis of dihydropyrimidinethione podand in the presence of l-proline or 4-hydroxy-l-proline and metal nitrates
Filatova, E. S.
Fedorova, O., V
Ovchinnikova, I. G.
Chistyakov, K. A.
Rusinov, G. L.
Charushin, V. N.
RUSSIAN CHEMICAL BULLETIN, 2022, 71 (07) : 1506 - 1513
[7] THE STRUCTURE OF DICHLORO(4-HYDROXY-L-PROLINE)CADMIUM(II)
YUKAWA, Y
INOMATA, Y
TAKEUCHI, T
SHIMOI, M
OUCHI, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (10) : 3135 - 3137
[8] Nanosized metal or silicon oxides and L-proline or 4-hydroxy-L-proline in stereoselective synthesis of a dihydropyrimidinethione podand
Filatova, Elena S.
Fedorova, Olga V.
Ovchinnikova, Irina G.
Chistyakov, Konstantin A.
Ganebnykh, Ilya N.
Uimin, Mikhail A.
Rusinov, Gennady L.
APPLIED ORGANOMETALLIC CHEMISTRY, 2023, 37 (07)
[9] ORDERED STRUCTURES IN SEQUENTIAL COPOLYPEPTIDES CONTAINING L-PROLINE OR 4-HYDROXY-L-PROLINE
MATTICE, WL
MANDELKERN, L
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (17) : 5285 - +
[10] A formal synthesis of a muscarinic M1 receptor antagonist, (-)-TAN1251A
Mizutani, H
Takayama, J
Soeda, Y
Honda, T
HETEROCYCLES, 2004, 62 : 343 - 355

← 1 2 3 4 5 →