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- W2950256538 abstract "Abstract A novel method has been developed for the synthesis of (±)-17-methoxy-hexadehydroyonimbane ( 11 ) which could be converted to yohimbinoid alkaloids through a sequence of reactions. The approach for the desired synthesis was based on the choice of 6-methoxy-3-isochromanone ( 9 ) as a suitable synthon for the construction of non-nitrogeneous moiety. The nitrogeneous portion was developed from tryptamine. An appropriate condensation of 9 and tryptamine yielded (±)-17-methoxy-hexadehydroyohimbane. 6-Methoxy-3-isochromanone ( 9 ) which is a δ-lactone was prepared from 5-methoxy-2-indanone ( 3 ) by Baeyer-Villiger oxidation. A simple procedure for the synthesis of 3 has been developed by a unique acid catalysed diazoketone cyclisation. It deserves mention in this connection that the acid catalyzed cyclization was facile with 3-methoxy-benzyl diazomethyl ketone ( 8 ) but 4-methoxybenzyl diazomethyl ketone ( 2 ) was reluctant to cyclize. All attempts in this direction resulted in the formation of a hydroxy ketone ( 4 ) as a major product." @default.
- W2950256538 created "2019-06-27" @default.
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- W2950256538 date "1988-02-09" @default.
- W2950256538 modified "2023-10-05" @default.
- W2950256538 title "ChemInform Abstract: Synthetic Entry into Yohimbinoid Alkaloids and Novel Synthesis of (.+-.)-17-Methoxy-hexadehydroyohimbane" @default.
- W2950256538 cites W2086379235 @default.
- W2950256538 doi "https://doi.org/10.1002/chin.198806307" @default.
- W2950256538 hasPublicationYear "1988" @default.
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