Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol

被引：29

作者：

Das, Subhendu ^{[1
]}

Kuilya, Tapan Kumar ^{[1
]}

Goswami, Rajib Kumar ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 12期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; WACKER OXIDATION; FORMAL SYNTHESIS; DIHYDROXYLATION; CONDENSATION; DERIVATIVES; ALDEHYDES; EPOXIDES; SULFONES; REVISION;

D O I：

10.1021/acs.joc.5b00972

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and convergent route for stereoselective total synthesis of promising anticancer natural lipid mycalol has been achieved using cheap and readily available L-arabinose as a chiral pool. The notable features of our synthesis comprised regioselective Wacker oxidation, Sharpless asymmetric dihydroxylation, Julia-Kocienski olefination, Wittig olefination, Zipper reaction, and Sonogashira reaction. Comparison of the spectroscopic data on a series of isomers supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.

引用

页码：6467 / 6489

页数：23

共 42 条

[11] Total synthesis of (-)-mucocin [J].

Crimmins, Michael T. ;

Zhang, Yan ;

Diaz, Frank A. .

ORGANIC LETTERS, 2006, 8 (11) :2369-2372

[12] Formal Synthesis of (+)-Sorangicin A [J].

Crimmins, Michael T. ;

Haley, Matthew W. ;

O'Bryan, Elizabeth A. .

ORGANIC LETTERS, 2011, 13 (17) :4712-4715

[13] Asymmetric Total Synthesis of Pyranicin [J].

Crimmins, Michael T. ;

Jacobs, Danielle L. .

ORGANIC LETTERS, 2009, 11 (12) :2695-2698

[14] Mycalol: A Natural Lipid with Promising Cytotoxic Properties against Human Anaplastic Thyroid Carcinoma Cells [J].

Cutignano, Adele ;

Nuzzo, Genoveffa ;

D'Angelo, Daniela ;

Borbone, Eleonora ;

Fusco, Alfredo ;

Fontana, Angelo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9256-9260

[15] Stereoselective Total Synthesis of Marine Cyclodepsipeptide Calcaripeptides A-C [J].

Das, Sayantan ;

Goswami, Rajib Kumar .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9778-9791

[16] Stereoselective Total Synthesis of leodomycins A and B and Revision of the NMR Spectroscopic Data of leodomycin B [J].

Das, Sayantan ;

Goswami, Rajib Kumar .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7274-7280

[17]

de la Pradilla RF, 1998, J ORG CHEM, V63, P9612

[18] Total Synthesis of the Anti-Apoptotic Agents Iso- and Bongkrekic Acids [J].

Francais, Antoine ;

Leyva, Antonio ;

Etxebarria-Jardi, Gorka ;

Ley, Steven V. .

ORGANIC LETTERS, 2010, 12 (02) :340-343

[19] Total Synthesis of Clathculins A and B [J].

Hoye, Rebecca C. ;

Anderson, Gretchen L. ;

Brown, Susan G. ;

Schultz, Erica E. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7400-7403

[20]

JULIA M, 1973, TETRAHEDRON LETT, P4833

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