Olefinic nitrone and nitrile oxide [3+ 2] cycloadditions. A short stereospecific synthesis of biotin from cycloheptene

…, D Lollar-Confalone, MR Uskokovic

Index: Confalone, Pat N.; Pizzolato, Giacomo; Confalone, Dianne Lollar; Uskokovic Milan R. Journal of the American Chemical Society, 1980 , vol. 102, # 6 p. 1954 - 1960

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Citation Number: 64

Abstract

Abstract: A novel synthesis of biotin (6) from cycloheptene (4) via the key amino alcohol 5 is described. The synthetic scheme is based upon an intramolecular nitrone-olefin [3+ 21 cycloaddition of the reactive intermediate 13, generated in situ from the aldehyde 12. The resulting isoxazolidine 14 is produced stereospecifically with the correct relative stereochemistry for elaboration into the target molecule. An even more efficient route ...