Stereoselective Total Synthesis of (S)-(+)-α-Curcumene

Abstract

Abstract: A facile stereoselective synthetic route to (S)-(+)-α-curcumene 1 was achieved by employing asymmetric dihydroxylation and reduction by Raney Ni in situ. After three steps, the key intermediates 7a and 7b were obtained. They were subjected the to reduction by AlHCl 2 to result in (S)-(+)-α-curcumene (1) in a high enantioselectivity and high yield. In the protective step of compounds 7a and 7b with MsCl in the presence of NEt 3, the elimination reaction and rearrangement were found and the corresponding diene 8 was afforded and elucidated by NMR method.

Key words: Bisabolane, Sesquiterpene, (S)-(+)-α-Curcumene, Stereoselectivity, Diasteromer

CLC Number:

O625

TrendMD:

LI An-Pai, LI Yang, DU Zhen-Ting, SHE Xue-Gong, PAN Xin-Fu . Stereoselective Total Synthesis of (S)-(+)-α-Curcumene[J]. Chem. J. Chinese Universities, 2004, 25(5): 862.

References

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