38 Gambierolの合成研究(口頭発表の部)
スポンサーリンク
概要
- 論文の詳細を見る
Since 1981, a number of polycyclic ethers have been isolated from marine dinoflagellates. Much attention has been paid to the synthesis of these compounds due to their unusual structures, biological activities, and the rarity in nature. Gambierol, which has a 6,6,6,6,7,6,6,7-polycyclic ether skeleton including 18 stereocenters and a triene side chain, was isolated from the cultured cells of Gambierdiscus toxicus by Yasumoto in 1993. The compound shows toxicity against mice (LD_<50> 50μg/kg), and the symptoms resemble those caused by ciguatoxins inferring the possibility that it is also implicated in ciguatera poisoning. We now report the stereocontrolled construction of the AB, E, and H ring systems of Gambierol as parts of its total synthetic study. First, synthesis of the AB ring system of gambierol was achieved from 2-deoxy-D-ribose. The key steps were the stereoselective allylation of the aldehyde 2, corresponding to the B ring, and the intramolecular hetero-Michael reaction of 5. Next, the synthesis of the E ring was accomplished from D-ribose via the intramolecular reaction of allylic stannane 24 as a key step. The undesired stereoisomer 26 formed in this reaction was converted to the desired product 33 by using DBU mediated isomerization. Finally, stereoselective synthesis of the H ring was achieved from 2-deoxy-D-ribose by using the intramolecular reaction of allylic stannane 43 as a key step. Modified Stille coupling was successfully applied for the construction of the triene side chain to give 57.
- 天然有機化合物討論会の論文
- 1998-08-31
著者
関連論文
- 26 ガンビ***ールの合成研究(口頭発表の部)
- 41 ポリ環状エーテルの収束的合成とガンビ***ール全合成への応用(口頭発表の部)
- 1P171 Oxygen binding properties of hemoglobins from diving mammals(5. Heme protein,Poster Session,Abstract,Meeting Program of EABS & BSJ 2006)
- Influence of a Single Amide Group on the Redox Function of Pseudomonas aeruginosa Cytochrome c_
- P-31 ブレベトキシンBの全合成(ポスター発表の部)
- 37(D-7) ブレベトキシンBの合成研究(口頭発表の部)
- 119(P62) ポリ環状エーテルの立体選択的合成とその応用(ポスター発表の部)
- Characterization of Non-Native Heme Coordination Structures Emerging upon Guanidine Hydrochloric Acid-Induced Unfolding of Pseudomonas aeruginosa Ferricytochrome c_
- ホウ素元素を導入した新しい酵素阻害剤の開発に関する研究 (平成14年度専門研究会報告書「中性子捕捉療法システムの高度化」)
- π-アリルパラジウム錯体を用いる有機合成のルネッサンス
- 99 中性子捕捉療法による癌治療のためのホウ素キャリアーの設計と合成(ポスター発表の部)
- Inclusion Complexation of 4-Biphenylcarboxylate, 4-Biphenylacetate, and 4-Biphenylsulfonate with α-Cyclodextrin, Studied by Pulse Radiolysis
- Determination of Association Constants for Cyclodextrin Inclusion Complexation by Pulse Radiolysis
- ^FNMR Study on the Heme Electronic Structure in Oxy and Carbonmonoxy Reconstituted Myoglobins
- ^FNMR Study of the Heme Orientation and Electronic Structure in a Myoglobin Reconstituted with a Ring-Fluorinated Heme
- 11 14族有機金属化合物を用いる新規環化反応の開発とポリエーテル系天然物合成への応用(口頭発表の部)
- 38 Gambierolの合成研究(口頭発表の部)
- Reduction-Alkylation with Organocopper(I) Reagents-Alkyl Halides : Highly Regioselective α-Alkylation of γ-Acetoxy-α, β-enoates with Lithium Dibutylcuprate-Alkyl Halides and Difference in the Reactivity of Electron-Deficient Olefins with Organocopper(I)-L
- Characterization of the acid-alkaline transition in the individual subunits of human adult and foetal methaemoglobins
- Heme Is Not Required for Aquifex aeolicus Cytochrome c_ Polypeptide Folding
- Correlation between the Stability and Redox Potential of Three Homologous Cytochromes c from Two Thermophiles and One Mesophile
- Lewis Acid-Catalyzed Hydrometalation and Carbometalation of Unactivated Alkynes
- 有機銅-ルイス酸複合剤の最近の展開
- 全合成 (特集 21世紀の化学--残された大テ-マ 逆説"The End of Chemistry")
- 有機金属ルイス酸複合系
- アリルスズの分子内反応を用いるポリ環状エーテルおよび関連ヘテロ環化合物の立体選択的合成
- 24 ヘミブレベトキシンBの全合成(口頭発表の部)
- 有機銅を用いた不斉誘起反応
- Determination of Oxygen Binding Properties of the Individual Subunits of Intact Human Adult Hemoglobin
- Field-dependent ^F NMR study of sperm whale myoglobin reconstituted with a ring-fluorinated heme
- 38 ブレベナールの全合成(口頭発表の部)