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Zur Synthese des Ecdysons. IV. Mitteilung über Insektenhormone . Die Synthese des natürlichen Häutungshormons
Author(s) -
Kerb U.,
Schulz G.,
Hocks P.,
Wiechert R.,
Furlenmeier A.,
Fürst A.,
Langemann A.,
Waldvogel G.
Publication year - 1966
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19660490519
Subject(s) - chemistry , hydroxylation , stereochemistry , tetrahydropyran , ecdysone , ether , metalation , ring (chemistry) , organic chemistry , hormone , enzyme , biochemistry
Ecdysone ( 9 ), a hormone responsible for the skin shedding process of arthropoda , has been synthesized. (20 S )‐2β,3β‐Diacetoxy‐20‐formyl‐5β‐pregn‐7‐en‐6‐one was prepared from the corresponding carboxylic acid and converted into ecdysone by a G RIGNARD reaction with 2‐methyl‐3‐butyn‐2‐ol tetrahydropyran‐2‐yl ether, followed by hydrogenation of the triple bond, removal of the protecting groups, and hydroxylation in the 14α‐position. C‐22‐isoecdysone was obtained as a by‐product.