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Synthesis of 2-Fluoro Analogues of Frontalin (2000)

Bravo, Pierfrancesco ; Frigerio, Massimo ; Ono, Taizo ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1387-1389

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ISSN: 1434-193X

Keywords: Natural products ; Epoxidations ; Asymmetric synthesis ; Fluorine ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---The synthesis of enantiomerically and diastereomerically pure (-)-(1R,2R,5R)- and (-)-(1R,2S,5R)-2-fluoro frontalin (7) starting from (+)-(1S)-menthyl-(R)-toluene-4-sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4-pentenyl bromide and diazomethane is described. The absolute stereochemistry was unambiguously determined by X-ray analysis of (+)-(1S,2R,5S,RS)-5, an intermediate in the synthesis of the enantiomeric (+)-(1S,2R,5S)-2-fluoro frontalin (7).

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

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