A Direct Catalytic Asymmetric Aldol Reaction of a-Sulfanyl Lactones: Efficient Synthesis of SPT Inhibitors

被引：28

作者：

Takechi, Sho ^{[1
,2
]}

Yasuda, Shigeo ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 17期

关键词：

aldol reaction; asymmetric catalysis; silver; SPT inhibitor; sulfanyl lactone; VIRIDIOFUNGIN-A; ALDEHYDES; KETONES; COMPLEXES; THIOAMIDES; TRIESTER; PROLINE; ESTERS; AMIDES;

D O I：

10.1002/anie.201200520

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Softly does it: The title reaction, catalyzed by a AgPF 6/(R)- biphep-type ligand/DBU complex, is described (see scheme). This protocol gives efficient access to syn-configured α-sulfanyl-β-hydroxy lactones in a highly enantioselective manner. In one particular case, the sulfide group was stereospecifically replaced with a hydroxy group to afford an enantioenriched tertiary alcohol, which upon further manipulation led to a class of densely functionalized SPT inhibitors. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4218 / 4222

页数：5

共 51 条

[1]

Aoki M., 2004, PCT Int. Appl., Patent No. [WO 2004071503, 2004071503]

[2] Stereoselective total synthesis of serine palmitoyl-CoA transferase inhibitors [J].

Byun, Hoe-Sup ;

Lu, Xuequan ;

Bittman, Robert .

SYNTHESIS-STUTTGART, 2006, (15) :2447-2474

[3] THEORETICAL-ANALYSIS OF FACTORS DETERMINING CONFORMATIONS AND STABILITIES OF OXYCARBANIONS AND THIOCARBANIONS [J].

EPIOTIS, ND ;

YATES, RL ;

BERNARDI, F ;

WOLFE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (18) :5435-5439

[4] Synthesis of viridiofungin A trimethyl ester and determination of the absolute structure of viridiofungin A [J].

Esumi, T ;

Iwabuchi, Y ;

Irie, H ;

Hatakeyama, S .

TETRAHEDRON LETTERS, 1998, 39 (08) :877-880

[5] Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates [J].

Evans, DA ;

Downey, CW ;

Hubbs, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) :8706-8707

[6] A Stereoselective Synthesis of (-)-Viridiofungin A Utilizing a TiCl4-Promoted Asymmetric Multicomponent Reaction [J].

Ghosh, Arun K. ;

Kass, Jorden .

ORGANIC LETTERS, 2012, 14 (02) :510-512

[7] A simple, short, and flexible synthesis of viridiofungin derivatives [J].

Goldup, Stephen M. ;

Pilkington, Christopher J. ;

White, Andrew J. P. ;

Burton, Andrew ;

Barrett, Anthony G. M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6185-6191

[8] ISOLATION AND STRUCTURE ELUCIDATION OF VIRIDIOFUNGIN-A, VIRIDIOFUNGIN-B AND VIRIDIOFUNGIN-C [J].

HARRIS, GH ;

JONES, ETT ;

MEINZ, MS ;

NALLINOMSTEAD, M ;

HELMS, GL ;

BILLS, GF ;

ZINK, D ;

WILSON, KE .

TETRAHEDRON LETTERS, 1993, 34 (33) :5235-5238

[9] CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].

ITO, Y ;

SAWAMURA, M ;

HAYASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6405-6406

[10] Direct Catalytic Enantio- and Diastereoselective Aldol Reaction of Thioamides [J].

Iwata, Mitsutaka ;

Yazaki, Ryo ;

Chen, I-Hon ;

Sureshkumar, Devarajulu ;

Kumagai, Naoya ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (14) :5554-5560

← 1 2 3 4 5 6 →