Synthetic approach toward the total synthesis of kempane diterpenes via transannular Diels-Alder strategy

Franck Caussanel; Keyan Wang; Sreekanth A Ramachandran; Pierre Deslongchamps

doi:10.1021/jo061230k

Synthetic approach toward the total synthesis of kempane diterpenes via transannular Diels-Alder strategy

J Org Chem. 2006 Sep 15;71(19):7370-7. doi: 10.1021/jo061230k.

Authors

Franck Caussanel¹, Keyan Wang, Sreekanth A Ramachandran, Pierre Deslongchamps

Affiliation

¹ Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.

PMID: 16958532
DOI: 10.1021/jo061230k

Abstract

Total syntheses of two new (+/-)-kempane derivatives 30 and 47 were achieved with transannular Diels-Alder reaction (TADA) serving as the key step for the stereoselective formation of tricyclic [6.6.5] system 3. This synthetic approach also reveals that the geometry of the C3 group of such a tricyclic system plays an important role for the formation of the seven-membered kempane skeleton.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cyclization
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / isolation & purification
Isoptera / chemistry
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry
Macrocyclic Compounds / isolation & purification
Molecular Structure

Substances

Diterpenes
Macrocyclic Compounds