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An Improved Method for the endo-Fusion of Five-Membered Ring Lactones to the Bornane Ring System (1998)

Knollmüller, Max ; Gärtner, Peter ; Ferencic, Mathias ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2507-2511

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ISSN: 1434-193X

Keywords: Camphoracetyl chloride ; Lactols, fused ; Lactones, fused ; Pseudoacid chlorides ; Reagents, stereoselective ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: endo-Fused lactone 3 was obtained in high yield from the camphoracetic acid 2 with thionyl chloride and a subsequent reduction of intermediate 5 with tributyltin hydride. The structure of 5 was elaborated and some aspects of the mechanism of its formation and reactivity were investigated. Lactone 3 serves as key intermediate for lactol 1 which is a useful reagent in racemate resolution and asymmetric synthesis.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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