156723-09-0Relevant articles and documents
Synthesis of (±)- and (+)-perovskone
Majetich, George,Zhang, Yong,Tian, Xinrong,Britton, Jonathan E.,Li, Yang,Phillips, Ryan
experimental part, 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.
Concise synthesis of (±)-perovskone
Majetich, George,Zhang, Yong
, p. 4979 - 4980 (2007/10/02)
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