Synthesis of 10-Halogenated Clavulone Derivatives

Synthesis of 10-Halogenated Clavulone Derivatives

Expoxidation of clavulone II (1) with tert-butyl hydroperoxide gave stereoselectively the epoxide 2. Reaction of 2 with lithium chloride gave effectively the 10-chlorinated clavulone derivative 3a. The brominated derivative 3b and iodinated derivative 3c were also synthesized from 2. The 10-fluorina...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1989/05/25, Vol.37(5), pp.1173-1175
Hauptverfasser: IGUCHI, Kazuo, KANETA, Soichiro, TSUNE, Chieko, YAMADA, Yasuji
Format: Artikel
Sprache:eng
Schlagworte:
10, 11-epoxyclavulone II
10-halogenated clavulone derivative
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
clavulone II
Exact sciences and technology
lithium halide
marine prostanoid
Organic chemistry
potassium hydrogen difluoride
Preparations and properties
Prostaglandins
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Zusammenfassung:Expoxidation of clavulone II (1) with tert-butyl hydroperoxide gave stereoselectively the epoxide 2. Reaction of 2 with lithium chloride gave effectively the 10-chlorinated clavulone derivative 3a. The brominated derivative 3b and iodinated derivative 3c were also synthesized from 2. The 10-fluorinated derivative 3d was synthesized by the reaction of 2 with potassium hydrogen difluoride.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.37.1173