Natürlich vorkommende Terpen-Derivate, 70. Synthese des 5,8-Dehydro-4-oxonerolidols

✍ Scribed by Bohlmann, Ferdinand ;Krammer, Robert

• Publisher: Wiley (John Wiley & Sons)
• Year: 1976
• Tongue: English
• Weight: 172 KB
• Volume: 109
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19761091012

✦ Synopsis

Eingegangen am 11. Februar 1976

Ausgehend von dem C6-Acetylenalkohol 1 erhalt man das Keton 6. Umsetzung von 6 mit Vinylmagnesiumbromid, &xfiuhrung in die Saure 12 und deren Reaktion rnit 2-Methyl-1-propenyllithium ergibt das Keton 14, das in allen spektroskopischen Daten rnit denen des Naturstoffs iibereinstimmt.

Naturally Occurring Terpene Derivatives, 701)

Synthesis of 5,8-Dehydro-4-oxonerolidol

Starting. with the C,-acetylenic alcohol 1 the ketone 6 has been obtained. Reaction of 6 with vinylmagnesium bromide, transformation into the acid 12, and reaction of the latter with 2-methyl-I-propenyllithium afford the ketone 14, which is in agreement in all spectroscopic data with those of the natural compound.