In an effort to duplicate in the laboratory the natural processes that resemble the cyclization of 2,3-oxidosqualene,
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In an effort to duplicate in the laboratory the natural processes that resemble the cyclization of 2,3-oxidosqualene, chemists in 1970 and 1980 carried out the conversions shown in Fig. P17.51. Give a curved-arrow mechanism for each. (For purposes of this problem, let the acid and base catalysts be a general acid A—H and its conjugate base A¯.)
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(a) (b) Me Me AcO Me HO. Me DURA H Figure P17.51 Me Me -OH Me Me Me Me anor Me -Me 2,4,6-trinitrophenol (picric acid) MeNO BF3/EtO CHCl 75 HO AcO Me Me 1" Me Me OH " H M Me Me Me H Opp Me HO Me Me Me
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