Synthesis and Structure Revision of Nakiterpiosin

被引：108

作者：

Gao, Shuanhu ^{[1
]}

Wang, Oiaoling ^{[1
]}

Chen, Chuo ^{[1
]}

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 04期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; PHOTO-NAZAROV CYCLIZATION; NOR-D-HOMOSTEROIDS; AROMATIC KETONES; ALDOL REACTION; REARRANGEMENT; VERATRAMINE; ALDEHYDES; ORGANOSTANNANES; CYCLOPAMINE;

D O I：

10.1021/ja808110d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This manuscript describes a convergent synthesis and the revision of the relative stereochemistry of nakiterpiosin, a marine C-nor-D-homosteroid. Our synthesis features a late-stage carbonylative Stille cross-coupling reaction and a photo-Nazarov cyclization reaction that deliver the complete nakiterpiosin skeleton efficiently.

引用

页码：1410 / +

页数：4

共 70 条

[1] DIRECT CONVERSION OF ORGANIC HALIDES TO ALDEHYDES WITH CARBON-MONOXIDE AND TIN HYDRIDE CATALYZED BY PALLADIUM [J].

BAILLARGEON, VP ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (24) :7175-7176

[2]

BINNS W, 1968, CANCER RES, V28, P2323

[3] STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .7. USE OF THE TRIMETHYLSILYL GROUP AS A REMOVABLE STEREOCONTROL ELEMENT TO PROVIDE GREATLY ENHANCED LEVELS OF DIASTEREOSELECTION [J].

BOECKMAN, RK ;

BARTA, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3421-3423

[4] The Hedgehog signaling pathway as a target for anticancer drug discovery [J].

Borzillo, GV ;

Lippa, B .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2005, 5 (02) :147-157

[5] SYNTHESIS OF DIARYLKETONES THROUGH CARBONYLATIVE COUPLING [J].

BRUNET, JJ ;

CHAUVIN, R .

CHEMICAL SOCIETY REVIEWS, 1995, 24 (02) :89-95

[6] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[7] Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened [J].

Chen, JK ;

Taipale, J ;

Cooper, MK ;

Beachy, PA .

GENES & DEVELOPMENT, 2002, 16 (21) :2743-2748

[8]

Chen L, 2004, CHINESE J CHEM, V22, P984

[9] Teratogen-mediated inhibition of target tissue response to Shh signaling [J].

Cooper, MK ;

Porter, JA ;

Young, KE ;

Beachy, PA .

SCIENCE, 1998, 280 (5369) :1603-1607

[10] IRIDIUM COMPOUNDS IN CATALYSIS [J].

CRABTREE, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (09) :331-338

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