Efficient syntheses of yuehchukene and .beta.-(dehydroprenyl)indole

Autor:	Yua Kuang Chen, Yen Long Vincent Hong, Jyh-Horng Sheu
Rok vydání:	1993
Předmět:	Indole test Yuehchukene Acid catalysis chemistry.chemical_compound chemistry Diene Bicyclic molecule Yield (chemistry) Organic Chemistry Organic chemistry Alcohol Quinone
Zdroj:	The Journal of Organic Chemistry. 58:5784-5787
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00073a044
Popis:	Yuehchukene (1) has been synthesized by one-step transformations of both alcohols (E)-β-(3-hydroxy-3-methylbutenyl)indole (3) and β-(1-hydroxy-3-methylbut-3-enyl)indole (4) under various reaction conditions. Alcohol 3 can be prepared efficiently from indole-3-carboxaldehyde (8) via a two-step reaction sequence. Alcohol 4, an isomer of 3, can be obtained from the same starting material 8 in only one step. Alcohol 4 can be converted directly into β-(dehydroprenyl)indole (2) in high yield under mild conditions via a base-induced dehydration. However, alcohol 3 does not give diene 2 under the same reaction conditions. Since diene 2 has been used as the key intermediate for the syntheses of yuehchukene (1) , analogues of 1, and a cytotoxic compound, murrapanine (7), our present work also completes formal total syntheses of these bioactive compounds
Databáze:	OpenAIRE
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