Synthetic studies on a picrotoxane sesquiterpene, coriamyrtin. III. Completion of the stereococtrolled total synthesis of (.+-.)-coriamyrtin.

• 田中 圭

• 内山 文昭

• 坂元 清志

• 犬伏 康夫

抄録

The stereocontrolled total synthesis of (±)-coriamyrtin (1) has now been completed, starting from protoanemonin and 2-methyl-1, 3-cyclopentanedione, through fifteen steps. The Wittig reaction of the ditetrahydrofuranyl ether (3) with triphenylphosphonium methylide gave the exo-methylenic compound (4), which was derived to the lactone (6) by consecutive hydrolysis, alkaline hydrolysis, and lactonization. The lactone (6) was transformed into the bromoether (8), which was subjected to allylic hydroxylation to give the allyl alcohol (10). Epoxidation of the allyl alcohol (10) provided selectively the epoxy-alcohol (11), which was derived to the mesylate (16). Elimination of the O-mesyl group gave the olefin (17). Epoxidation of 17 with m-chloroperbenzoic acid gave (±)-bromocoriamyrtin (18) and finally, reductive debromination of 18 furnished (±)-coriamyrtin (1).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 31 (6), 1972-1979, 1983

  公益社団法人 日本薬学会

キーワード

• debromination

詳細情報

• CRID: 1390001204165325696
• NII論文ID: 130003769365
• DOI: 10.1248/cpb.31.1972
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/31/6/31_6_1972/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可