- Enantioselective synthesis of 4-heterosubstituted cyclopentenones
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Racemic 4-hydroxycyclopentenone, readily derived from furfuryl alcohol, can be transformed via its O-Boc derivative to 4-acyloxy, 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladium-catalyzed kinetic resolution via nucleophilic allylic substitutions. Applying this methodology, a short formal synthesis of ent-noraristeromycin was readily accomplished.
- Ulbrich, Kathrin,Kreitmeier, Peter,Vilaivan, Tirayut,Reiser, Oliver
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p. 4202 - 4206
(2013/06/04)
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- SYNTHESIS OF 10-HALOGENATED CLAVULONE DERIVATIVES
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Epoxidaton 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
- Iguchi Kazuo,Kaneta, Soichiro,Tsune, Chieko,Yamada, Yasuji
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p. 1173 - 1175
(2007/10/02)
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