A protecting group free and scalable approach towards total synthesis of (-)-venlafaxine

被引：14

作者：

Chavan, Subhash P. ^{[1
]}

Pawar, Kailash P. ^{[1
]}

Garai, Sumanta ^{[1
]}

机构：

[1] CSIR NCL Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

RSC ADVANCES | 2014年 / 4卷 / 28期

关键词：

ANTIDEPRESSANT; EPOXIDATION; ENANTIOMERS; RESOLUTION;

D O I：

10.1039/c4ra00840e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A protecting group free asymmetric total synthesis of (-)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (-)-venlafaxine.

引用

页码：14468 / 14470

页数：3

共 22 条

[1] Novel δ2-isoxazolines as group II phospholipase A2 inhibitors [J].

Basappa ;

Kumar, MS ;

Swamy, SN ;

Mahendra, M ;

Prasad, JS ;

Viswanath, BS ;

Rangappa, KS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3679-3681

[2] Asymmetric synthesis of both the enantiomers of antidepressant venlafaxine and its analogues [J].

Bhuniya, Rajib ;

Nanda, Samik .

TETRAHEDRON LETTERS, 2012, 53 (15) :1990-1992

[3] Ligand-accelerated vanadium-catalysed epoxidation in water [J].

Bourhani, Z ;

Malkov, AV .

CHEMICAL COMMUNICATIONS, 2005, (36) :4592-4594

[4]

Chavan S. P., 2003, US Patent, Patent No. [US 6,504,044B2, 6504044, US 6504044 B2]

[5]

Chavan S. P., 2002, CHEM ABSTR, Patent No. US 6, 350, 912B1

[6]

Chavan S. P., 2007, SYNTHETIC COMMUN, V37, P2007

[7] An efficient and green protocol for the preparation of cycloalkanols: a practical synthesis of venlafaxine [J].

Chavan, SP ;

Khobragade, DA ;

Kamat, SK ;

Sivadasan, L ;

Balakrishnan, K ;

Ravindranathan, T ;

Gurjar, MK ;

Kalkote, UR .

TETRAHEDRON LETTERS, 2004, 45 (39) :7291-7295

[8] Asymmetric total synthesis of (-)-venlafaxine using an organocatalyst [J].

Chavan, Subhash P. ;

Garai, Sumanta ;

Pawar, Kailash P. .

TETRAHEDRON LETTERS, 2013, 54 (17) :2137-2139

[9] Enantioselective synthesis of β-amino esters and its application to the synthesis of the enantiomers of the antidepressant Venlafaxine [J].

Davies, Huw M. L. ;

Ni, Aiwu .

CHEMICAL COMMUNICATIONS, 2006, (29) :3110-3112

[10]

DOLITZKY BZ, 2005, Patent No. 6924393

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