82890-07-1Relevant academic research and scientific papers
Synthesis of Macrocyclic Terpenoids by Intramolecular Carbonyl Coupling: Flexibilene and Humulene
McMurry, John E.,Matz, James R.,Kees, Kenneth L.
, p. 5489 - 5498 (1987)
Total syntheses of two macrocyclic sesquiterpene hydrocarbons, humulene (1) and flexibilene (2) are discussed in detail.Both were prepared in high overall yield by titanium-induced cyclization of the appropriate keto aldehyde precursors (4 and 9, respectively), themselves obtained by coupling of the vinylic zirconium reagent 22 with pi-allylpalladiums 26 and 23.
SYNTHESIS OF FLEXIBILENE, A NATURALLY OCCURING 15-MEMBERED-RING DITERPENE
McMurry, John,Matz, James R.,Kees, Kenneth L.,Bock, Peter A.
, p. 1777 - 1780 (2007/10/02)
A total synthesis of the naturally occuring 15-membred ring diterpene, flexibilene, was accomplished using a titanium-induced cyclization of the keto-aldehyde 3,3,7,11-tetramethyl-15-oxohexadeca-4E,7E,11E-trienal as the key step.
