Studies on the Syntheses of Heterocyclic Compounds and Natural Products. CMXCII. Synthesis of an A-Homograyanotoxane and a Phyllocladane Ring System from a Common Precursor

Studies on the Syntheses of Heterocyclic Compounds and Natural Products. CMXCII. Synthesis of an A-Homograyanotoxane and a Phyllocladane Ring System from a Common Precursor

Thermolysis of 5-[(n-butylthio) methylene]-2-[2-(1-cyano-5-methoxybenzocyclobutenyl)-ethyl]-3-methylcyclopentanone (16) gave the tetracyclic compound (18) in excellent yield, and 18 was transformed into both the A-homograyanotoxane (3) and the phyllocladane (4) ring systems.

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1983/01/25, Vol.31(1), pp.57-63
Hauptverfasser: SHISHIDO, KOZO, MATSUURA, TAKAHIRO, FUKUMOTO, KEIICHIRO, KAMETANI, TETSUJI
Format: Artikel
Sprache:eng
Schlagworte:
Wagner-Meerwein rearrangement
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Zusammenfassung:Thermolysis of 5-[(n-butylthio) methylene]-2-[2-(1-cyano-5-methoxybenzocyclobutenyl)-ethyl]-3-methylcyclopentanone (16) gave the tetracyclic compound (18) in excellent yield, and 18 was transformed into both the A-homograyanotoxane (3) and the phyllocladane (4) ring systems.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.31.57