A convenient synthesis of 25-deoxyecdysone, a major secretory product of crustacean Y-organs and of 2,25-dideoxyecdysone, its putative immediate precursor.
25-Deoxyecdysone, a major secretory product of Y-organs of at least several species of crustaceans and the immediate precursor of circulating ponasterone A in these animals, can easily be synthesized from ecdysone. The present four-step procedure involves the formation of a mixture of delta 24,25 and delta 25,26 intermediates which might also be used to prepare a labeled reference compound for metabolic or binding studies. Similarly, 2,25-dideoxyecdysone was prepared from 2-deoxyecdysone. These compounds have been used to identify metabolites of [3H]-2,22,25-trideoxyecdysone (= 5 beta-ketodiol) formed by Y-organs of the shore crab, Carcinus maenas.
Pis
J
J
Ecole Normale Supérieure, Département de Biologie, Paris, France.
Girault
J P
JP
Larchevêque
M
M
Dauphin-Villemant
C
C
Lafont
R
R
D000818:Animals; D003386:Brachyura / Q000737:chemistry*; D002783:Cholestenones / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004440:Ecdysone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004702:Endocrine Glands / Q000378:metabolism*; D015394:Molecular Structure; D012621:Seasons
C094721:2,25-dideoxyecdysone; D002783:Cholestenones; C079152:25-deoxyecdysone; D004440:Ecdysone; C007424:3 beta,14 alpha-dihydroxy-5 beta-cholest-7-en-6-one