Synthesis of substances related to gibberellins part XV A partial synthesis of gibberellin C
β Scribed by Kenji Mori; Masanao Matsui; Yusuke Sumiki
- Publisher
- Elsevier Science
- Year
- 1964
- Tongue
- French
- Weight
- 218 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
SINCE the total syntheaia of (f)-glbberlc1*2 and (*I-epigibberic2 acids had been accompllshed , our efforts were directed to the synthesis of gibbane compounda containing the lha-lactone bridge which is characteristic to all gibbere111ns. We now rlsh to describe a partial synthesis of gibberellln C (Ij3, a biologically active lactonic acid obtained from gibberellin Al. A diketo ester (11j4, m.p. 107-108oC, timax. (Nujol) 1736, X Part XIV, K. Mori, M. Ratsui and Y. Sumiki, Agr. Biol. Chem. (Tokyo), 28, 243 (1964). *% Biochemical Studies on "Bakanae" Funaus. Part 72. This is a part of a paper read at the 3rd I.U.P.A.C. International Spmposium on the Chemietry of Natural Products held in Kyoto, Japan, in April, 1964.
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BIOCHEMICAL STUDIES ON "BAKANAE" FUNGUS. PART 75. SYNTHESIS OF SUBSTANCES RELATED TO GIBBERELLINS.
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The epimeric gibberellin-A 7-aldehydes 1 and 2 were silylated, enolised with KH and 3labelled with -3 H20 to give after desilylation the tritium-labelled epimeric gibberellin-A ?-aldehydes 2 and 2. Subsequent acetylation, oxidation and deacetylation afforded [ 6-3H] gibberellin-A3 (6) and [ 6-3H]6-e
of Sciences of the GDR, DDR-8051 Dresden, German Democratic Republic s u m y The pbytohomone gibberellin-A was tritium-labell d by a chemical route. The specific aativity o f the [ 6 d -3 H ]gibberellin-,; obtained was 22.5 Ci/nmol.