Asymmetric synthesis of (+)-preussin from N-sulfinyl δ-amino β-ketoesters

被引：35

作者：

Davis, FA ^{[1
]}

Deng, JH ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 23期

关键词：

D O I：

10.1016/j.tet.2004.03.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient asymmetric synthesis of the antifungal pyrrolidine alkaloid (+)-preussin (2) was accomplished via the stereoselective reduction of a 5-substituted 3-oxo proline. The oxo proline was prepared from an N-sulfinyl delta-amino beta-ketoester, a sulfinimine derived polyfunctionalized chiral building block. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5111 / 5115

页数：5

共 21 条

[1] Bach T, 1998, ANGEW CHEM INT EDIT, V37, P3400, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3400::AID-ANIE3400>3.0.CO
[2] 2-3
[3] A polymer-supported proline-based diamine catalyst for the kinetic resolution of racemic secondary alcohols
Clapham, B
Cho, CW
Janda, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) : 868 - 873
[4] Asymmetric synthesis of functionalized trans-2,6-disubstituted piperidines with N-Sulfinyl δ-amino β-ketoesters.: Synthesis of (-)-lasubine I
Davis, FA
Rao, A
Carroll, PJ
[J]. ORGANIC LETTERS, 2003, 5 (21) : 3855 - 3857
[5] Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion
Davis, FA
Yang, B
Deng, JH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) : 5147 - 5152
[6] Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich Cyclization and n-sulfinyl δ-amino β-ketoesters
Davis, FA
Mang, Y
Anilkumar, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) : 8061 - 8064
[7] Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
Davis, FA
Chao, B
Andemichael, YW
Mohanty, PK
Fang, TN
Burns, DM
Rao, A
Szewczyk, JM
[J]. HETEROATOM CHEMISTRY, 2002, 13 (05) : 486 - 492
[8] Asymmetric synthesis of substituted prolines from δ-amino β-ketoesters.: Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate
Davis, FA
Fang, TN
Goswami, R
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1599 - 1602
[9] Davis FA, 2000, SYNTHESIS-STUTTGART, P2106
[10] Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
Chao, B
Rao, A
[J]. ORGANIC LETTERS, 2001, 3 (20) : 3169 - 3171

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