Total synthesis of paracentrone, C31-allenic apo-carotenoid.
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.
Murakami
Yusuke
Y
School of Science and Technology, Kwansei Gakuin University, Sanda, Hyogo, Japan.
Nakano
Masayuki
M
Shimofusa
Takuya
T
Furuichi
Noriyuki
N
Katsumura
Shigeo
S
D000447:Aldehydes / Q000737:chemistry; D002338:Carotenoids / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; D007454:Iodides; C511164:paracentrone; D002338:Carotenoids