Synthesis of Molluscicidal Agent Cyanolide A Macrolactone from D-(-)-Pantolactone

被引：43

作者：

Hajare, Atul K. ^{[1
]}

Ravikumar, Velayutham ^{[1
]}

Khaleel, Shaik ^{[1
]}

Bhuniya, Debnath ^{[1
]}

Reddy, D. Srinivasa ^{[1
]}

机构：

[1] Advinus Therapeut Ltd, Discovery Chem, Pune 411057, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 03期

关键词：

NATURAL-PRODUCT (-)-CLAVOSOLIDE-A; SPONGE MYRIASTRA-CLAVOSA; ENANTIOSPECIFIC SYNTHESIS; ABSOLUTE-CONFIGURATION; SCHISTOSOMIASIS; BRYOSTATINS; REDUCTION; MACROLIDE; FRAGMENT; RING;

D O I：

10.1021/jo101782q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of potent molluscicidal agent cyanolide A, a glycosidic 16-membered macrolide, starting from D-(-)-pantolactone is reported. Highly stereoselective aldol, oxa-Michael addition, and Yamaguchi macrolactonization are the key steps in the present synthesis.

引用

页码：963 / 966

页数：4

共 39 条

[1]

[Anonymous], 1993, WHO TECHN REP SER, V830

[2]

[Anonymous], 1980, B WHO, V58, P681

[3] A stereoselective synthesis of the C(1)-C(16) fragment of the bryostatins [J].

Ball, M ;

Baron, A ;

Bradshaw, B ;

Omori, H ;

MacCormick, S ;

Thomas, EJ .

TETRAHEDRON LETTERS, 2004, 45 (47) :8737-8740

[4] Total synthesis of the marine natural product (-)-clavosolide A [J].

Barry, Conor S. ;

Elsworth, Jon D. ;

Seden, Peter T. ;

Bushby, Nick ;

Harding, John R. ;

Alder, Roger W. ;

Willis, Christine L. .

ORGANIC LETTERS, 2006, 8 (15) :3319-3322

[5] A century of schistosomiasis research [J].

Bergquist, Robert .

ACTA TROPICA, 2008, 108 (2-3) :65-68

[6] An Efficient Formal Synthesis of (-)-Clavosolide A Featuring a "Mismatched" Stereoselective Oxocarbenium Reduction [J].

Carrick, Jesse D. ;

Jennings, Michael P. .

ORGANIC LETTERS, 2009, 11 (03) :769-772

[7] Total synthesis of clavosolide A [J].

Chakraborty, Tushar Kanti ;

Reddy, Vakiti Ramkrishna ;

Gajula, Praveen Kumar .

TETRAHEDRON, 2008, 64 (22) :5162-5167

[8] The global status of schistosomiasis and its control [J].

Chitsulo, L ;

Engels, D ;

Montresor, A ;

Savioli, L .

ACTA TROPICA, 2000, 77 (01) :41-51

[9] Praziquantel [J].

Cioli, D ;

Pica-Mattoccia, L .

PARASITOLOGY RESEARCH, 2003, 90 (Suppl 1) :S3-S9

[10] A novel molluscicidal formulation of niclosamide [J].

Dai, Jian-Rong ;

Wang, Wei ;

Liang, You-Sheng ;

Li, Hong-Jun ;

Guan, Xiao-Hong ;

Zhu, Yin-Chang .

PARASITOLOGY RESEARCH, 2008, 103 (02) :405-412

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