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

[21] Stereoselective Total Syntheses of Leiocarpin A and (-)-Galantinic Acid Starting from D-Mannitol [J].

Nagaiah, Kommu ;

Sreenu, Domalapally ;

Purnima, Kamaraju V. ;

Rao, Ramisetti Srinivasa ;

Yadav, Jhillu S. .

SYNTHESIS-STUTTGART, 2009, (08) :1386-1392

[22] Stereoselective first total synthesis of (R)-rugulactone [J].

Reddy, D. Kumar ;

Shekhar, V. ;

Reddy, T. Srikhanth ;

Reddy, S. Purushotham ;

Venkateswarlu, Y. .

TETRAHEDRON-ASYMMETRY, 2009, 20 (20) :2315-2319

[23] The first stereoselective total synthesis of neosemburin and isoneosemburin [J].

Reddy, Gadi Madhusudhan ;

Sridhar, Perali Ramu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (42) :8408-8414

[24] A concise formal stereoselective total synthesis of (-)-swainsonine [J].

Wang, Xiao-Gang ;

Wang, Ai-E ;

Huang, Pei-Qiang .

CHINESE CHEMICAL LETTERS, 2014, 25 (02) :193-196

[25] An Efficient Stereoselective Total Synthesis of Aculeatins A and B [J].

Das, Biswanath ;

Krishnaiah, Martha ;

Nagendra, Siddavatam ;

Reddy, Cheruku R. .

LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (04) :244-248

[26] Facile Total Synthesis and Bioactivity of Aspernigerin [J].

Wu, Qinglai ;

Li, Yongqiang ;

Yang, Xinling ;

Ling, Yun .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (08) :1498-1502

[27] The stereoselective total synthesis of PF1163A [J].

Kumar, Harish ;

Reddy, A. Srinivas ;

Reddy, B. V. Subba .

TETRAHEDRON LETTERS, 2014, 55 (09) :1519-1522

[28] Efficient Stereoselective Total Synthesis of (+)-Cryptofolione and the First Synthesis of (-)-Cryptocaryalactone [J].

Balasubramanyam, P. ;

Reddy, Gandolla Chinna ;

Salvanna, Nayaki ;

Das, Biswanath .

SYNTHESIS-STUTTGART, 2011, (22) :3706-3710

[29] A facile stereoselective synthesis of (Z)-α-arylsulfonyl-α,β-unsaturated ketones [J].

You, Shengyong ;

Li, Jianying ;

Cai, Mingzhong .

TETRAHEDRON, 2009, 65 (34) :6863-6867

[30] A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin [J].

Reddy, K. Sridhar ;

Rao, B. Venkateswara .

TETRAHEDRON-ASYMMETRY, 2011, 22 (02) :190-194

← 1 2 3 4 5 →