Structure and Absolute Stereochemistry of the Anticancer Agent EBC-23 from the Australian Rainforest

被引：30

作者：

Dong, Lin ^{[1
]}

Gordon, Victoria A. ^{[3
]}

Grange, Rebecca L. ^{[1
]}

Johns, Jenny ^{[2
]}

Parsons, Peter G. ^{[2
]}

Porzelle, Achim ^{[1
]}

Reddell, Paul ^{[3
]}

Schill, Heiko ^{[1
]}

Williams, Craig M. ^{[1
]}

机构：

[1] Univ Queensland, Sch Mol & Microbial Sci, Brisbane, Qld, Australia

[2] PO Royal Brisbane Hosp, Queensland Inst Med Res, Brisbane, Qld, Australia

[3] EcoBiot Ltd, Yungaburra, Qld, Australia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 46期

关键词：

D O I：

10.1021/ja807133p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Louraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.

引用

页码：15262 / +

页数：3

共 30 条

[1] Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].

Aho, JE ;

Pihko, PM ;

Rissa, TK .

CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440

[2] Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue [J].

Albert, Brian J. ;

Sivaramakrishnan, Ananthapadmanabhan ;

Naka, Tadaatsu ;

Czaicki, Nancy L. ;

Koide, Kazunori .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (09) :2648-2659

[3] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].

CHEN, KM ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1987, 28 (02) :155-158

[4] ISOLATION, STRUCTURE DETERMINATION AND SYNTHESIS OF NEW DIHYDROISOCOUMARINS FROM GINKGO-BILOBA L [J].

CHOUKCHOUBRAHAM, N ;

ASAKAWA, Y ;

LEPOITTEVIN, JP .

TETRAHEDRON LETTERS, 1994, 35 (23) :3949-3952

[5] Enantioselective total synthesis of altohyrtin C (spongistatin 2) [J].

Evans, DA ;

Trotter, BW ;

Coleman, PJ ;

Côté, B ;

Dias, LC ;

Rajapakse, HA ;

Tyler, AN .

TETRAHEDRON, 1999, 55 (29) :8671-8726

[6] Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].

Evans, DA ;

Coleman, PJ ;

Dias, LC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741

[7]

FURSTNER A, 2007, J CHEM SOC CHEM COMM, V304, P5

[8] Concise asymmetric syntheses of radicicol and monocillin I [J].

Garbaccio, RM ;

Stachel, SJ ;

Baeschlin, DK ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10903-10908

[9] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[10]

Hashimoto T, 2002, HETEROCYCLES, V56, P581

← 1 2 3 →