Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL

Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL

A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1995/01/15, Vol.43(1), pp.49-52
Hauptverfasser: FUJII, Tozo, OHBA, Masashi, SETO, Shigeki
Format: Artikel
Sprache:eng
Schlagworte:
Bischler-Napieralski cyclization
Chemistry
cincholoipon
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
lactim ether N-alkylation
Ophiorrhiza alkaloid synthesis
ophiorrhizine configuration
Organic chemistry
oxazolium hydrogenolysis
Preparations and properties
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Zusammenfassung:A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H2O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.43.49