156723-07-8Relevant 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.
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
experimental part, 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.
