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Published on: October 10, 2014
Total synthesis of paracentrone, C31-allenic apo-carotenoid
Yusuke Murakami1, Masayuki Nakano, Takuya Shimofusa
1School of Science and Technology, Kwansei Gakuin University, Sanda, Hyogo, Japan.
Abstract:
The stereocontrolled total synthesis of a C31-allenic apo-carotenoid, paracentrone, was achieved by the convergent C20 + C11 = C31 strategy. The key elements of our synthesis were the Pd-catalyzed cross-coupling to stereoselectively construct the conjugated polyene backbone skeleton and the designed geometrical isomerization at the central double bond of the conjugated polyene chain. In addition, the terminal oxygenated cyclohexane ring having the allenic moiety was prepared by the highly diastereoselective Sharpless epoxidation under our own reaction conditions.
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