Anticancer Agents from the Australian Tropical Rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76

被引：33

作者：

Dong, Lin ^{[1
]}

Schill, Heiko ^{[1
]}

Grange, Rebecca L. ^{[1
]}

Porzelle, Achim ^{[1
]}

Johns, Jenny P. ^{[2
]}

Parsons, Peter G. ^{[2
]}

Gordon, Victoria A. ^{[3
]}

Reddell, Paul W. ^{[3
]}

Williams, Craig M. ^{[1
]}

机构：

[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia

[2] EcoBiotics Ltd, Yungaburra, Qld 4884, Australia

[3] PO Royal Brisbane Hosp, Queensland Inst Med Res, Brisbane, Qld 4029, Australia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 42期

关键词：

anticancer agents; Australian tropical rainforests; natural products; total synthesis; RING-CLOSING-METATHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; COMPLEX NATURAL-PRODUCTS; C SPONGISTATIN 2; MITSUNOBU REACTION; TERMINAL EPOXIDES; CONSTRUCTION; STRATEGIES; LACTONES; SPIROKETALS;

D O I：

10.1002/chem.200901525

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8% overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze-Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell fine DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.

引用

页码：11307 / 11318

页数：12

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