Easy Access to (E)-β-Ocimene

被引：15

作者：

Yildizhan, Selma ^{[1
]}

Schulz, Stefan ^{[1
]}

机构：

[1] TU Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany

来源：

SYNLETT | 2011年 / 19期

关键词：

terpenoids; Grignard reaction; alkenes; hydrocarbons; coupling; INSECT HERBIVORY; MECHANISM; ALCOHOLS;

D O I：

10.1055/s-0031-1289869

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Ocimene is one of the most common monoterpenes found in Nature, but a simple and reliable synthesis of the pure E-isomer has been missing. Here, we report a simple procedure involving a Grignard coupling as the key step that allows its synthesis on gram scales. The configuration of the double bond is fixed in the starting material.

引用

页码：2831 / 2833

页数：3

共 23 条

[21] Chromatography with silver nitrate [J].

Williams, CM ;

Mander, LN .

TETRAHEDRON, 2001, 57 (03) :425-447

[22] Isopentenyl diphosphate isomerase. Mechanism-based inhibition by diene analogues of isopentenyl diphosphate and dimethylallyl diphosphate [J].

Wu, Z ;

Wouters, J ;

Poulter, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17433-17438

[23] HIGHLY STEREOSPECIFIC PROCEDURE FOR THE TRANSFORMATION OF ALLYLIC ALCOHOLS INTO 1,3-DIENES [J].

YASUDA, A ;

TANAKA, S ;

YAMAMOTO, H ;

NOZAKI, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (06) :1752-1756

← 1 2 3 →