The Total Synthesis of (-)-Nitidasin

被引：30

作者：

Hog, Daniel T. ^{[1
,2
]}

Huber, Florian M. E. ^{[1
,2
]}

Mayer, Peter ^{[1
,2
]}

Trauner, Dirk ^{[1
,2
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Univ Munich, Ctr Integrated Prot Sci, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 32期

关键词：

ring-closing olefin metathesis; sesterterpenoids; stereoselective; synthesis; total synthesis; GLYCOSYLPHOSPHATIDYLINOSITOL-ANCHORING INHIBITOR; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PALLADIUM-CATALYZED ALLYLATION; TRANSITION-METAL CATALYSIS; RING-CLOSING METATHESIS; CARBON BOND FORMATION; CONSTRUCTION; STEREOCHEMISTRY; NITIOL; ASTELLATOL;

D O I：

10.1002/anie.201403605

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine "Hercampuri". It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox

引用

页码：8513 / 8517

页数：5

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