Synthesis of d-biotin from L-cystine via intramolecular [3+ 2] cycloaddition

…, HL Lee, G Pizzolato, MR Uskokovic

Index: Baggiolini, Enrico G.; Lee, Hsi Lin; Pizzolato, Giacomo; Uskokovic, Milan R. Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6460 - 6462

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Citation Number: 55

Abstract

In summary the zinc chloride-THF catalyst system would appear to have exhibited all of the characteristics to be expected of the pericyclic (type a) model. The required intermediate type, 3, is produced in a stereospecific reaction. No acyclic intermediates are observed. Strict suprafaciality, in addition to the diene, is apparently followed. The selective endo orientation of the diene has been rationalized? Finally, the trans&-diene 11 reacts much ...