Total Synthesis of Racemic Laurenditerpenol, an HIF-1 Inhibitor

被引：38

作者：

Jung, Michael E. ^{[1
]}

Im, G-Yoon Jamie ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90064 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 22期

基金：

美国国家科学基金会;

关键词：

CYCLIC MESO-ANHYDRIDES; DIELS-ALDER REACTIONS; CINCHONA ALKALOIDS; PRIMARY ALCOHOLS; CANCER-THERAPY; DEOXYGENATION; ANALOGS; DESYMMETRIZATION; ZOANTHAMINE; FRAGMENTS;

D O I：

10.1021/jo902029x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The convergent total synthesis of the HIF-1 inhibitor laurenditerpenol 1 and its diastereomer 1' is reported. The key step involves the Julia-Kocienski olefination-reduction process between the sulfone 55 and the aldehyde 54. The unusual trimethylated oxanorbornane sulfone 55 was successfully synthesized from the known exo Diels-Alder adduct 24 of 2,5-dimethylfuran 7 and maleic anhydride 23 in 8 steps. The aldehyde 54 was prepared by ring-opening and elaboration of lactone 41. In addition, four analogues of I were also successfully synthesized for biological testing.

引用

页码：8739 / 8753

页数：15

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