ISOLATION AND STEREOCONTROLLED SYNTHESIS OF A 17-HYDROXY-16-BETA,17-DIHYDROGIBBERELLIN, GA(82)

Authors
SETO H SASSA T KAWAIDE H SHIGIHARA T UZAWA J YOSHIDA S
Citation
H. Seto et al., ISOLATION AND STEREOCONTROLLED SYNTHESIS OF A 17-HYDROXY-16-BETA,17-DIHYDROGIBBERELLIN, GA(82), Tetrahedron letters, 36(33), 1995, pp. 5917-5920
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
33
Year of publication
1995
Pages
5917 - 5920
Database
ISI
SICI code
0040-4039(1995)36:33<5917:IASSOA>2.0.ZU;2-Z
Abstract
A 17-hydroxy-16 beta,17-dihydrogibberellin, GA(82) 9, was first isolat ed from a fungus, Phaeosphaeria sp. L487, and was synthesized from nat urally abundant GA(4) 1 in a highly stereocontrolled manner whose esse ntial step was inversion of C(16) configuration of readily accessible 16 beta-formyl intermediate 5 to more stable 16 alpha-epimer 6 by base treatment.