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Total synthesis of (±)-gibberellic acid

✍ Scribed by Hiroto Nagaoka; Masanao Shimano; Yasuji Yamada

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
309 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Total synthesis of (*t_)-gibberellic acid was accomplished via highly stereocontrolled route. A number of synthetic efforts for Cl9 -gibberellin phytohormones have been made in recent years. ' The total synthesis of gibberellic acid (gibberellin A3, GA3), a representative gibberellin, was completed first by Corey et al. 2 -and then by Mander et al. 3 However, --intensive work is still being made for the establishment of a more efficient method of the synthesis of Clg-gibberellins. 4

Here, we describe a highly stereocontrolled total synthesis of (f)-GA3, in fcgYo H 11 "&Q which tetrahydrofluorene derivative z5 previously synthesized was converted into enone 6 having the same 5 B 8' 01, 6 --OH C (9) configuration as in GA3, then the D-ring system H D

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