A Convergent and Stereoselective Total Synthesis of Phomolides G and H

被引：7

作者：

Reddy, B. V. Subba ^{[1
]}

Reddy, P. Sivaramakrishna ^{[1
]}

Reddy, B. Phaneendra ^{[1
,2
]}

Yadav, J. S. ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

[2] Yogi Vemana Univ, Dept Chem, Kadapa 516003, Andhra Pradesh, India

来源：

SYNLETT | 2014年 / 25卷 / 04期

关键词：

MacMillan asymmetric epoxidation; ring-closing metathesis; decalactones; RING-CLOSING METATHESIS; MARINE-DERIVED FUNGUS; 10-MEMBERED LACTONES; STAGONOSPORA-CIRSII; CHOLESTEROL-BIOSYNTHESIS; POTENTIAL MYCOHERBICIDE; SECONDARY METABOLITES; FAMILY; DECARESTRICTINES; MICROCARPALIDE;

D O I：

10.1055/s-0033-1340348

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of phomolides G and H, a polyketide natural products is described. The synthesis involves organocatalytic enantioselective asymmetric epoxidation, C1-Wittig olefination, and ring-closing metathesis as key steps. The use of organocatalytic MacMillan asymmetric epoxidation for the construction of two chiral centers of phomolides G and H makes this approach more attractive.

引用

页码：501 / 504

页数：4

共 30 条

[1] NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].

ALCARAZ, L ;

HARNETT, JJ ;

MIOSKOWSKI, C ;

MARTEL, JP ;

LEGALL, T ;

SHIN, DS ;

FALCK, JR .

TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452

[2] Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation [J].

Amatore, Muriel ;

Beeson, Teresa D. ;

Brown, Sean P. ;

MacMillan, David W. C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5121-5124

[3] Multiplolides A and B, new antifungal 10-membered lactones from Xylaria multiplex [J].

Boonphong, S ;

Kittakoop, P ;

Isaka, M ;

Pittayakhajonwut, D ;

Tanticharoen, M ;

Thebtaranonth, Y .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (07) :965-967

[4] Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction [J].

Crimmins, MT ;

She, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) :12790-12791

[5] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

[6] Decanolides, 10-membered lactones of natural origin [J].

Drager, G ;

Kirschning, A ;

Thiericke, R ;

Zerlin, M .

NATURAL PRODUCT REPORTS, 1996, 13 (05) :365-375

[7] Stagonolides G-I and Modiolide A, Nonenolides Produced by Stagonospora cirsii, a Potential Mycoherbicide for Cirsium arvense [J].

Evidente, Antonio ;

Cimmino, Alessio ;

Berestetskiy, Alexander ;

Andolfi, Anna ;

Motta, Andrea .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11) :1897-1901

[8] Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsium arvense [J].

Evidente, Antonio ;

Cimmino, Alessio ;

Berestetskiy, Alexander ;

Mitina, Galina ;

Andolfi, Anna ;

Motta, Andrea .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (01) :31-34

[9]

GOHRT A, 1992, J ANTIBIOT, V45, P66

[10] SECONDARY METABOLITES BY CHEMICAL-SCREENING .8. DECARESTRICTINES, A NEW FAMILY OF INHIBITORS OF CHOLESTEROL-BIOSYNTHESIS FROM PENICILLIUM .1. STRAIN DESCRIPTION, FERMENTATION, ISOLATION AND PROPERTIES [J].

GRABLEY, S ;

GRANZER, E ;

HUTTER, K ;

LUDWIG, D ;

MAYER, M ;

THIERICKE, R ;

TILL, G ;

WINK, J ;

PHILIPS, S ;

ZEECK, A .

JOURNAL OF ANTIBIOTICS, 1992, 45 (01) :56-65

← 1 2 3 →