Tetrahedron p. 1237 - 1244 (1980)
Update date:2022-08-04
Topics:
Lischewski, M.
Adam, G.
Reaction sequences leading to GA3 derivatives with stepwise deoxygenated position 7 have been reported.From four different methods studied for the synthesis of GA3-7-alcohols the direct NaBH4-reduction of the anhydrides 5a and 5b has been found to be optimal leading in good yields to 3 and 9, respectively.Oxidation of 3 with the N-chlorosuccinimide-dimethylsulfide complex or pyridinium chlorochromate followed by deacetylation afforded the GA3-7-aldehyde (16).-The partial synthesis of 6β-methyl-7-nor-GA3 (20) has been realized starting from 3 via the iodinemethyl compound 18 and its reduction with (C2H5)3SnH or Na2
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