A new synthetic strategy for natural triquinanes is presented as a model study. Stereospecific rearrangement of the ready accessible bicyclo[3.3.1] nonanic acetoxychloride 6 gave the cis-pentalanic hydroxyaldehyde 5, which has been converted into the ketone 4 already reported as a key intermediate in some syntheses of the title capnellenes.
Gambacorta, A., Fabrizi, G., Bovicelli, P. (1992). BICYCLO[3.3.1]NONANE APPROACH TO TRIQUINANES - FORMAL SYNTHESIS OF (+/-)-DELTA-9(12)CAPNELLENE AND (+/-)-DELTA-9(12)CAPNELLENE-8-BETA-10-ALPHA-DIOL. TETRAHEDRON, 48(21), 4459-4464 [10.1016/S0040-4020(01)80453-1].
BICYCLO[3.3.1]NONANE APPROACH TO TRIQUINANES - FORMAL SYNTHESIS OF (+/-)-DELTA-9(12)CAPNELLENE AND (+/-)-DELTA-9(12)CAPNELLENE-8-BETA-10-ALPHA-DIOL
GAMBACORTA, Augusto;
1992-01-01
Abstract
A new synthetic strategy for natural triquinanes is presented as a model study. Stereospecific rearrangement of the ready accessible bicyclo[3.3.1] nonanic acetoxychloride 6 gave the cis-pentalanic hydroxyaldehyde 5, which has been converted into the ketone 4 already reported as a key intermediate in some syntheses of the title capnellenes.File in questo prodotto:
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