156723-06-7Relevant articles and documents
Synthesis of (±)- and (+)-perovskone
Majetich, George,Zhang, Yong,Tian, Xinrong,Britton, Jonathan E.,Li, Yang,Phillips, Ryan
, p. 10129 - 10146 (2012/02/03)
A biomimetic synthesis of the triterpene (±)-perovskone was achieved featuring a remarkable polycyclization process in which three rings, four bonds, and five stereocenters were created in a single operation in 82% yield. This convergent synthesis required 16 steps, starting from vanillin, and proceeded in 9% overall yield. A second route to prepare optically active quinone 2 took 15 steps in 36% overall yield and featured a palladium-catalyzed reductive allylic transposition to establish the C-5 chirality stereospecifically. Quinone (-)-2 was converted to (+)-perovskone (1) via a polycyclization cascade, which created four rings, five bonds, and six stereocenters in a single operation in 50% yield.
Ga(IIl)-catalyzed cycloisomerization approach to (±)-icetexone and (±)-epi-icetexone
De Jesus Cortez, Felipe,Sarpong, Richmond
supporting information; experimental part, p. 1428 - 1431 (2010/07/03)
"Chemical eqation presented" A Ga(III)-catalyzed cycloisomerization reaction provides expedient access to a benzannulated cycloheptadiene bearing a cyano group, which has been applied to the syntheses of several icetexane diterpenoids including icetexone
Total synthesis of (+)-19-deoxyicetexone, (-)-Lcetexone, and (+)-5-epi-icetexone
Majetlch, George,Grove, Jeremy L.
supporting information; experimental part, p. 2904 - 2907 (2009/12/06)
The first asymmetric total syntheses of 19-deoxylcetexone, Icetexone, and 5-epl-Icetexone was achieved from eplmerlc tricyclic dlenes.
Total synthesis of (±)-komaroviquinone
Majetich, George,Lift, Yang,Zou, Ge
scheme or table, p. 217 - 225 (2009/09/06)
(±)-Komaroviquinone (1) was synthesized from 3,4,5-trimethoxybenzoic acid in twenty-two steps. The key transformations in this synthesis are: (1) the construction of the cycloheptane ring via a Friedel-Crafts cyclialkylation; (2) a regiospecific benzylic oxidation; (3) a conformationally controlled introduction of the C(10) hydroxyl group and (4) intramolecular hemi-acetal formation.
A formal total synthesis of salvadione
Maier, Martin E.,Bayer, Alexander
, p. 4034 - 4043 (2007/10/03)
The tricyclic 6-7-6 core structure of the triterpene salvadione (1) was obtained in an efficient manner from the aryl bromide 16 and the alkyl iodide 35 carrying a methylenecyclohexane group at the terminus. Alkylation of the anion derived from 16 with th
Stereoselective syntheses of (±)-komaroviquinone and (±)-faveline methyl ether through intramolecular Heck reaction
Sengupta, Sujaya,Drew, Michael G. B.,Mukhopadhyay, Ranjan,Achari, Basudeb,Banerjee, Asish Kr
, p. 7694 - 7700 (2007/10/03)
An efficient, flexible, and stereoselective convergent route for constructing the trans-10-hydroxy-1,1-dimethyloctahydrodibenzo[a,d]cyclohepten- 7-ones (5a-c) was achieved via intramolecular Heck reaction. This strategy has been successfully implemented for the syntheses of (±)-komaroviquinone (3) through (±)-coulterone dimethyl ether (5c) and (±)-faveline methyl ether (1a).