19 新規三量体型インドールアルカロイドpsychotrimineの全合成(口頭発表の部)

• 松田 洋平

  千葉大院薬

• 北島 満里子

  千葉大院薬

• 高山 廣光

  千葉大院薬

書誌事項

タイトル別名

• 19 Total Synthesis of New Trimeric Indole Alkaloid, Psychotrimine

抄録

A number of polymeric Nb-methyltryptamine-derived alkaloids that link together two to eight pyrrolidinoindoline units have been isolated from rubiaceous plants. Some of them have a variety of biological activities involving potent opioid agonistic activity. Recently, we have investigated the alkaloidal constituents in Psychotria rostrata native to Malaysian rainforest and have found three novel tryptamine-derived alkaloids, named pscyhotrimine (1). psychotetramine (2) and psychopentamine (3). To establish their structures as well as to develop the efficient synthetic route, we embarked on the total synthesis of these structurally unique alkaloids. 1. Total synthesis of new trimeric alkaloid, psychotrimine All the hitherto known tryptamine-related polymeric alkaloids are composed of pyrrolidinoindoline units and link together at the C3a-C3a' and C3a-C7' positions. Characteristically, psychotrimine (1) is the first example of this class of alkaloid that contains the tryptamine unit in the molecule as well as possesses the linkage at C3a-Na (indole) and C7-Na (indole) positions. We planned a synthetic strategy that employs the copper mediated intramolecular and intermolecular amination of halobenzenes as key steps. Starting from 2-bromobenzaldehyde and indoline, we prepared dimeric compound (10) via intramolecular amination of amidine (8). Onto the C7 position of indoline core in 12, an additional tryptamine unit was installed by intermolecular amination to furnish the total synthesis of (±)-1. Here, we have proven the structure of psychotrimine. 2. Synthetic study of new tetrameric alkaloid, psychotetramine Psychotetramine (2) is a new tetrameric tryptamine-derived alkaloid containing the known dimeric alkaloid, chimonanthine, in the lower segment and one tryptamine unit in the upper part. To reveal the structure inferred by spectroscopic analyses, we planned the convergent strategy that involved the copper mediated intermolecular amination between iodide (12) and the stereoisomers of chimonanthine, the later of which have been synthesized by oxidative coupling of tryptamine derivatives with hypervalent iodine (III) reagent.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 49 (0), 109-114, 2007

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390001206078004736
• NII論文ID: 110006682749
• DOI: 10.24496/tennenyuki.49.0_109
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可