Stereoselective Reactions. XII. : Synthesis of Antitumor-Active Steganacin Analogs, Picrosteganol and Epipicrosteganol, by Selective Isomerization

New steganacin analogs with definite absolute configurations, (-)-picro- and (-)-epipicrosteganol, were synthesized by isomerization of (-)-steganol and (-)-episteganol, respectively, at the α-position to the lactone carbonyl. The structure of (-)-epipicrosteganol was confirmed by X-ray crystallogra...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1986/04/25, Vol.34(4), pp.1501-1504
Hauptverfasser:	TOMIOKA, KIYOSHI, ISHIGURO, TSUNEO, IITAKA, YOICHI, KOGA, KENJI
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemical synthesis Antineoplastic Agents, Phytogenic - chemical synthesis Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Furans - chemical synthesis Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemical synthesis Lignans Molecular Conformation Organic chemistry Organic compounds Physics Preparations and properties Stereoisomerism Structure of solids and liquids crystallography Structure of specific crystalline solids X-ray analysis X-Ray Diffraction
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Zusammenfassung:	New steganacin analogs with definite absolute configurations, (-)-picro- and (-)-epipicrosteganol, were synthesized by isomerization of (-)-steganol and (-)-episteganol, respectively, at the α-position to the lactone carbonyl. The structure of (-)-epipicrosteganol was confirmed by X-ray crystallographic analysis. Selective epimerization at the C-4 benzylic position was observed upon acidic treatment of (-)-steganacin, giving (-)-episteganacin.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.34.1501