Synthesis of panaxytriol and its stereoisomers as potential antitumor drugs

An efficient synthesis of panaxytriol and its seven stereoisomers was achieved, and four unnatural diastereomers of 2a were prepared. The key steps involved the opening of vicinal hydroxy epoxides, the stereospecific opening of the epoxides with perchloric acid, and the Cadiot–Chodkiewicz cross-coupling of chiral terminal alkynes with bromoalkynes. Preliminary antitumor activity investigations indicated that some synthetic panaxytriols exhibited promising cytotoxic activity against three human cancer cell lines.

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(3R,9R,10R)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = −18.1 (c 1.1, CHCl3)Absolute configuration: (3R,9R,10R)

(3R,9S,10S)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = −43.9 (c 1.1, CHCl3)Absolute configuration: (3R,9S,10S)

(3R,9R,10S)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = −31.6 (c 1.1, CHCl3)Absolute configuration: (3R,9R,10S)

(3R,9S,10R)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = −28.6 (c 0.8, CHCl3)Absolute configuration: (3R,9S,10R)

(3S,9R,10R)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = +50.0 (c 0.7, CHCl3)Absolute configuration: (3S,9R,10R)

(3S,9S,10S)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = +19.1 (c 0.7, CHCl3)Absolute configuration: (3S,9S,10S)

(3S,9R,10S)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = +29.4 (c 0.8, CHCl3)Absolute configuration: (3S,9R,10S)

(3S,9S,10R)-Heptadeca-1-en-4,6-diyne-3,9,10-triolC17H26O3[α]D20 = +29.0 (c 0.8, CHCl3)Absolute configuration: (3S,9S,10R)