Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates

被引：16

作者：

Yadav, Jhillu Singh ^{[1
]}

Das, Saibal ^{[1
]}

Mishra, Anand Kumar ^{[1
]}

机构：

[1] Indian Inst Chem Technol CSIR, Div Organ Chem 1, Hyderabad 500607, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 20期

关键词：

STYRYL-LACTONES; (+)-9-DEOXYGONIOPYPYRONE; (+)-ALTHOLACTONE; (+)-8-ACETYLGONIOTRIOL; 8-METHOXYGONIODIOL; (+)-GONIOFUFURONE; (+)-GONIOPYPYRONE; CYTOTOXICITY; DERIVATIVES; GONIODIOL;

D O I：

10.1016/j.tetasy.2010.08.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective synthesis of (+)-goniodiol a cytotoxic styryllactone has been accomplished in 10 steps starting from inexpensive and readily available D-manitol and delta-gluconolactone involving the direct and straightforward reaction conditions of Grignard addition chain elongation and hydroboration thus making the synthesis simple and convenient (C) 2010 Published by Elsevier Ltd

引用

页码：2443 / 2447

页数：5

共 50 条

[11] Concise Stereoselective Total Synthesis of Leiocarpin C [J].

Rao, Dasireddi Chandra ;

Shekhar, Vanam ;

Reddy, Dorigondla Kumar ;

Chinnababu, Baggu ;

Venkateswarlu, Yenamandra .

HELVETICA CHIMICA ACTA, 2013, 96 (12) :2179-2184

[12] Stereoselective total synthesis of (-)-curvularin [J].

Radha Krishna, Muniganti ;

Sridhar, Gattu ;

Syed, Tasqeeruddin ;

Jayaprakash, H. V. .

SYNTHETIC COMMUNICATIONS, 2022, 52 (01) :37-42

[13] Stereoselective total synthesis of cochliomycin A [J].

Wang, Linlin ;

Gao, Yangguang ;

Liu, Jun ;

Cai, Chao ;

Du, Yuguo .

TETRAHEDRON, 2014, 70 (16) :2616-2620

[14] Stereoselective Total Synthesis of (±)-Pleurospiroketals A and B [J].

Thorat, Sagar S. ;

Krishna, Gamidi Rama ;

Kontham, Ravindar .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19) :13572-13582

[15] Stereoselective Total Synthesis of (±)-Alstoscholarisine E [J].

Wood, Michael D. ;

Klosowski, Daniel W. ;

Martin, Stephen F. .

ORGANIC LETTERS, 2020, 22 (03) :786-790

[16] Stereoselective Total Synthesis of Polyrhacitides A and B [J].

Yadav, J. S. ;

Rajendar, Goreti .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (33) :6781-6788

[17] A New Stereoselective Total Synthesis of Phomonol [J].

Reddy, Basi V. Subba ;

Srinivas, Lavudia ;

Reddy, Pathuri Sivaramakrishna ;

Reddy, Bhemavarapu Phaneendra ;

Prasad, Attaluri R. ;

Yadav, Jhillu S. .

HELVETICA CHIMICA ACTA, 2014, 97 (10) :1326-1332

[18] Stereoselective total synthesis of amicoumacin C [J].

Suzuki, Tomomi ;

Nagasawa, Tomohiro ;

Enomoto, Masaru ;

Kuwahara, Shigefumi .

TETRAHEDRON, 2015, 71 (13) :1992-1997

[19] A concise stereoselective total synthesis of (+)-artemisinin [J].

Yadav, J. S. ;

Thirupathaiah, B. ;

Srihari, P. .

TETRAHEDRON, 2010, 66 (11) :2005-2009

[20] Asymmetric synthesis of (+)-altholactone: A styryllactone isolated from various goniothalamus species [J].

Enders, Dieter ;

Barbion, Julien .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (09) :2842-2849

← 1 2 3 4 5 →