Synthesis of trans--Elemene

Highly efficient syntheses of the anti-cancer agent trans--elemene have been achieved by using the readily available (+/-)-limonene as starting material. The syntheses were achieved in only nine to eleven steps with good overall yields. The key step in these reaction sequences is a stereoselective r...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2018; no. 35; pp. 4926 - 4932
Main Authors Benito Iglesias, D., Herrero Teijon, P., Rubio Gonzalez, Rosa, Fernandez-Mateos, A.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.09.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SESQUITERPENE COMPOSITION
C-13 NMR-SPECTRA
STEREOSPECIFIC SYNTHESIS
Radicals
STEREOSELECTIVE SYNTHESIS
BASIL OIL
Terpenoids
Natural products
DEOXYGENATION
Titanium
ASSIGNMENT
BETA-ELEMENE
CYCLIZATION
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Summary:Highly efficient syntheses of the anti-cancer agent trans--elemene have been achieved by using the readily available (+/-)-limonene as starting material. The syntheses were achieved in only nine to eleven steps with good overall yields. The key step in these reaction sequences is a stereoselective radical cyclization, induced by titanocene chloride.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800800