A Concise Catalytic Route to the Marine Sesquiterpenoids (-)-Clavukerin A and (-)-Isoclavukerin A

被引：27

作者：

Knueppel, Stephan ^{[1
]}

Rogachev, Victor O. ^{[1
]}

Metz, Peter ^{[1
]}

机构：

[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 32期

关键词：

Domino reactions; Metathesis; Michael addition; Organocatalysis; Ruthenium; Terpenoids; RING-CLOSING METATHESIS; TRINORGUAIANE SESQUITERPENE; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; CLAVUKERIN-A; EFFICIENT; (+/-)-CLAVUKERIN-A; ISOCLAVUKERIN; ALDEHYDES;

D O I：

10.1002/ejoc.201001087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products.

引用

页码：6145 / 6148

页数：4

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