Synthesis of Panax Acetylenes: Chiral Syntheses of Acetylpanaxydol, PQ-3 and Panaxydiol

Acetylpanaxydol (1-Ac), PQ-3 (2) and panaxydiol (3) and their optical isomers were synthesized from L-(+)-diethyl tartrate. The absolute configurations of 1-Ac, 2 and 3 were determined to be 1-Ac (3R,9R,10S), 2 (9R,10S) and 3 (3R,10S), respectively, by comparisons of their optical rotations and the...

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Veröffentlicht in:	Chemical & Pharmaceutical Bulletin 2004, Vol.52(4), pp.418-421
Hauptverfasser:	Satoh, Mitsuru, Watanabe, Mitsuo, Kawahata, Masatoshi, Mohri, Kunihiko, Yoshida, Yuki, Isobe, Kimiaki, Fujimoto, Yasuo
Format:	Artikel
Sprache:	eng
Schlagworte:	absolute configuration Acetylation Acetylene - analogs & derivatives Acetylene - chemical synthesis Alkynes - chemical synthesis Diynes enzyme mediated-acetylation Indicators and Reagents Magnetic Resonance Spectroscopy Oxidation-Reduction panax species panaxydiol panaxydol polyacetylene Stereoisomerism
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Zusammenfassung:	Acetylpanaxydol (1-Ac), PQ-3 (2) and panaxydiol (3) and their optical isomers were synthesized from L-(+)-diethyl tartrate. The absolute configurations of 1-Ac, 2 and 3 were determined to be 1-Ac (3R,9R,10S), 2 (9R,10S) and 3 (3R,10S), respectively, by comparisons of their optical rotations and the NMR data of their MTPA esters with those of natural products.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.52.418