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Bridged bicyclic ketal

In this reaction, considerable nitration of the tosyl groups was observed. The bicycle 89 was obtained in better yield (36%) from 88 by reaction with trifluoroacetyl nitrate in DCM <1996JOC8897, 1998LJSP5831099>. Swern oxidation of the dihydroxy diazocine 90a led to the oxygen-bridged hydroxyl diazocine 91 by transannular hemi-ketalization (Scheme 16) <1996JOC8897>. [Pg.333]

Martin has made ample use of this strategy for the synthesis of various polyketide natural products. Furan 164, prepared by addition of lithiofuran to a lactaldehyde derivative, gave the bridged ketal 165 upon oxidation and acid catalyzed dehydration <99T3561>. The bicyclic architecture allowed highly diastereoselective reactions which led to 166, a key intermediate for... [Pg.16]

See other pages where Bridged bicyclic ketal is mentioned: [Pg.87]    [Pg.87]    [Pg.54]    [Pg.217]    [Pg.647]    [Pg.68]    [Pg.155]    [Pg.688]    [Pg.302]    [Pg.222]    [Pg.222]   
See also in sourсe #XX -- [ Pg.129 ]



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