Study on Synthesis of anti-brassinosteroids

1989 Fiscal Year Final Research Report Summary

• Project/Area Number: 63560120
• Research Category: Grant-in-Aid for General Scientific Research (C)
• Allocation Type: Single-year Grants
• Research Field: 製造化学・食品
• Research Institution: The University of Tokyo
• Principal Investigator: YOKOTA Takao The University of Tokyo, Faculty of Agriculture, Lecturer, 農学部, 講師 (40011986)
• Co-Investigator(Kenkyū-buntansha): OKADA Katsuhide Yamagata University, Faculty of Education, Assistant Professor, 教育育学部, 助教授 (20011968)
• Project Period (FY): 1988 – 1989
• Keywords: steroid / brassinosteroid / anti-brassinosteroid / brassinolide / castasterone

Research Abstract

Brassinosteroids (BRs) are steroidal plant hormones of which importance has been recognized for these years. However, its basic function in plant growth has not yet been clarified. This research aims at the synthesis of BR antagonists which could be used as a tool to investigate functions of BRS. We attempted to synthesis the following two compounds.
1. Synthesis of compounds in which methyl groups are introduced. Stigmasterol was converted to 6,6-ethylenedioxystigmast-22-en-3- one using eight steps of reactions. The latter is reacted with methyl iodide under the presence of lithium diisopropylamide to give 2alpha-monomethyl, 2,2-dimethyl, 2alpha 4alpha -dimethyl derivatives. We are now attempting to introduce 22R, 23R-hydroxyls in these compounds using known reaction sequences.
2. Synthesis of a compound with thiirane in A ring. Stigmasterol was converted to 22S,23S-dihydroxystigmast-2-en-6-one using five reactions. We are now attempting to introduce thiirane in A ring.