Abstract
exo-exo-2,3,5,6-Bicyclo[2.2.1]heptanetetrol ( 5a) has been synthesized by treatment of bicyclo[2.2.1]hepta-2,5-diene with alkaline permanganate. The configurational assignment is based on ( a) analogy with similar reactions involving bicyclo[2.2.1]heptene, ( b) reactivity of the tetrol, and ( c) the n.m.r. spectra of the tetrol, three of its derivatives, and the corresponding 2,3-diol 2a and its derivatives. Long-range shielding and deshielding effects in these spectra are discussed. The influence of the tetrol on mitotic human and plant cells is noted.
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