Synthesis of the furanosteroidal antibiotic viridin

被引：107

作者：

Anderson, EA

Alexanian, EJ

Sorensen, EJ

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 15期

关键词：

cyclotrimerization; dihydroxylation; electrocyclic reactions; inhibitors; natural products;

D O I：

10.1002/anie.200353129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed alkyne cyclotrimerization, domino electrocyclic reactions, and a hydroxy-directed dihydroxylation are key steps in an efficient synthesis of the bioactive furanosteroid viridin (1) from a simple acyclic triyne.

引用

页码：1998 / 2001

页数：4

共 48 条

[1]

Adam G.C., 2003, ANGEW CHEM, V115, P5638

[2] (-)-FR182877 is a potent and selective inhibitor of carboxylesterase-1 [J].

Adam, GC ;

Vanderwal, CD ;

Sorensen, EJ ;

Cravatt, BF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5480-5484

[3] Proteomic profiling of mechanistically distinct enzyme classes using a common chemotype [J].

Adam, GC ;

Sorensen, EJ ;

Cravatt, BF .

NATURE BIOTECHNOLOGY, 2002, 20 (08) :805-809

[4] WORTMANNIN IS A POTENT PHOSPHATIDYLINOSITOL 3-KINASE INHIBITOR - THE ROLE OF PHOSPHATIDYLINOSITOL 3,4,5-TRISPHOSPHATE IN NEUTROPHIL RESPONSES [J].

ARCARO, A ;

WYMANN, MP .

BIOCHEMICAL JOURNAL, 1993, 296 :297-301

[5] STEREOSELECTIVITY OF ELECTROCYCLIC PROCESS, BENZOCYCLOBUTENE TO ORTHO QUINONE DIMETHIDE [J].

ARNOLD, BJ ;

SAMMES, PG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (18) :1034-&

[6] THE SYNTHESIS OF 10,10-DISUBSTITUTED ANTHRONES VIA THE REARRANGEMENTS OF 9-ANTHRYL ETHERS [J].

BRANZ, SE ;

CARR, JA .

SYNTHETIC COMMUNICATIONS, 1986, 16 (04) :441-451

[7] VIRIDIN - A HIGHLY FUNGISTATIC SUBSTANCE PRODUCED BY TRICHODERMA-VIRIDE [J].

BRIAN, PW ;

MCGOWAN, JC .

NATURE, 1945, 156 (3953) :144-145

[8] SYNTHETIC STUDIES ON WORTMANNIN AND 11-DESACETOXYWORTMANNIN [J].

BROKA, CA ;

RUHLAND, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4888-4894

[9] A SAFE AND EFFICIENT METHOD FOR CONVERSION OF 1,2-DIOLS AND 1,3-DIOLS TO CYCLIC CARBONATES UTILIZING TRIPHOSGENE [J].

BURK, RM ;

ROOF, MB .

TETRAHEDRON LETTERS, 1993, 34 (03) :395-398

[10] Chemical strategies for the global analysis of protein function [J].

Cravatt, BF ;

Sorensen, EJ .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (06) :663-668

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