Studies on a gibberellin synthesis
1971
Calton, Gary Jim
Routes leading to the synthesis of gibberellin A 13 have been studied. The addition of a functionalized carbene to form a bicyclo [3.2.1] octane ring system via 2,7-bisethlonedioxy-Δ⁹-octalin was attempted. A study of the functionalized carbenes was undertaken to determine their synthetic ability in such a synthetic procedure. Mass spectral studies of the octalin-2,7-dione system and its derivatives have been made. It was postulated that Δ⁹-octalin-2,7-dione undergoes an unusual hydrogen rearrangement resulting in the base peak at m/e 79. It was also found that Δ¹⁻⁹-octalin-2,7-dione under goes hydrogen rearrangement. The conditions necessary for efficient reduction of the above octalin systems was studied. It was found that methanol and 5% palladium on carbon at room temperature and atmospheric pressure resulted in the highest yield of cis and trans-decalin-2,7-dione. The synthesis of bicycle [3.2.1] octane via dihydroyangonole was attempted. Although it appeared that the product was formed, difficulty in the separations precluded positive identification of this compound.
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