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Zur Synthese des Ecdysons IX. Mitteilung über Insektenhormone
Author(s) -
Furlenmeier A.,
Fürst A.,
Langemann A.,
Waldvogel G.,
Hocks P.,
Kerb U.,
Wiechert R.
Publication year - 1967
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.19670500825
Subject(s) - chemistry , hydroxylation , stereospecificity , isomerization , tetrahydropyran , stereochemistry , ecdysone , side chain , ether , medicinal chemistry , organic chemistry , hormone , ring (chemistry) , catalysis , biochemistry , polymer , enzyme
A synthesis of ecdysone is described by which the insect moulting hormone can be readily prepared. Oxidation of ergosterol gave the 6‐keto‐Δ 7 ‐function, and preparation of the Δ 2 ‐olefine followed by stereospecific hydroxylation led to the 2β,3β‐glycol system. Ozonization furnished (20 S )‐2β,3β‐diacetoxy‐20‐formyl‐5α‐pregn‐7‐en‐6‐one into which the side chain was introduced by a Grignard reaction with 2‐methyl‐3‐butyn‐2‐ol tetrahydropyran‐2‐yl ether and a subsequent reduction of the triple bond. Hydroxylation at C‐14 and isomerization at C‐5 gave ecdysone. By an interchange of the sequence of the reactions C‐22 isoecdysone was obtained stereospecifically.