Short-Step Synthesis of Plant Growth-Promoting Brassinosteroids

• TAKATSUTO SUGURU

  Department of Chemistry, Tokyo Institute of Technology

• IKEKAWA NOBUO

  Department of Chemistry, Tokyo Institute of Technology

Abstract

Brassinolide analogues, (22R, 23R, 24R)-2α, 3α, 22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (24-epibrassinolide) (10) and (22S, 23S, 24R)-2α, 3α, 22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (9), were synthesized from brassicasterol (3a) in five steps and with ca. 20% overall yield. The key steps are the direct formation of (22E, 24R)-3α, 5-cyclo-5α-ergost-22-en-6-one (4) from brassicasterol mesylate (3b), the acid-catalyzed rearrangement of 4 to (22E, 24R)-5α-ergosta-2,22-dien-6-one (6), and the Baeyer-Villiger oxidation of the tetrahydroxy 5α-ergostan-6-ones 7 and 8.

Journal

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 32 (5), 2001-2004, 1984-05-25

  The Pharmaceutical Society of Japan

Keywords

• brassinolide
• brassinosteroid
• plant growth hormone
• brassicasterol
• Baeyer-Villiger oxidation

Details

• CRID: 1570572702508393216
• NII Article ID: 110003625008
• NII Book ID: AA00602100
• ISSN: 00092363
• Text Lang: en
• Data Source:
  • CiNii Articles