Journal fur Praktische Chemie - Chemiker-Zeitung p. 468 - 471 (1998)
Update date:2022-08-10
Topics:
Dilger, Ulrich
Franz, Baerbel
Roettele, Herbert
Schroeder, Gerhard
Herges, Rainer
Tropone is a structural unit of numerous natural products i.e. imerubrine, harringtonolide and colchicine (2). It is of interest to study the selectivity of formaldehyde-O-oxide (1) with respect to these polyfunctional tropone derivatives. We report about the reactions of 1 with colchicine (2) and the colchicine derivatives 5, 8, 11, 14, 17, 20 under ozone free conditions. The fragmentation of the spiroozonides 3, 6, 9, 12, 15, 18, 21 via the activated complexes 3a, 6a, 9a, 12a, 15a, 18a, 21a opens up an elegant route to the allocolchicines 4, 7, 10, 13, 16, 19. Johann Ambrosius Barth 1998.
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