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2002 Fiscal Year Final Research Report Summary

Enantioselective Total Synthesis of Marine Alkaloids Stellettamides

Research Project

Project/Area Number 13672235
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

YAMAZAK Inaoki  Tokyo University of Pharmacy and Life science, School of Pharmacy, Assistant Professor, 薬学部, 講師 (30277264)

Project Period (FY) 2001 – 2002
Keywords(+)-stellettamide A / (-)-stellettamide B / (1S,4S,8aR)-stellettamide C / marine sponge / calmodulin inhibitor / antifungal activity / ( R )-2-(1-aminoethyl)phenol / nitrogen containing natural products
Research Abstract

Stellettamid A was first isolated by Fustian in 1990 from a marine sponge of the genus Stelletta collected in Shikinejima of Japan as the first representive of an indolizidine class of marine alkaloids. Subsequently, Shin reported the isolation of the closely related alkaloid stellettamide B from a Korean specimen of Stelletta. Very recently, another alkaloid, stellettamide C was isolated from the Japanese sponge. Stellettamides A-C comprise a common indolizidine skeleton, containing a quaternary nitrogen atom and a variation of the unsaturated side chain, which are connected via an amide linkage. The present investigations were aimed at the first asymmetric total synthesis of stellettamides A, B, and C in an enatiomerically pure form utilizing asymmetric allylation of the chiral N-acyl-N, O-acetal
The tricyclic N-acyl-N, O-acetal incorporating ( R )-2-(1-aminoethyl)phenol as a chiral auxiliary underwent TiCl_4-mediated allylation to give the chiral allylpiperidinone with retention of configuration in high yield and diastereoselectivity. The first total synthesis of (+)-stellettamide A has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)indolizidine fragment, prepared from the (6R)-allylpiperidinone, with the chiral trienoic acid fragment. By employing the same methodology, the syntheses of (-)-stellettamide B and (1S,4S,8aR)-stellettamide C have been achieved. The synthesis of stelletamide B led to revision of the published relative stereochemistry of the natural product and established its absolute stereochemistry to be 1S,4S,8aR,6"R

  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] Naoki Yamazaki, Wataru, Dokoshi, Chihiro Kibayashi: "Total Synthesis of (-)-Stellettamide B and Determination of Its Absolute Stereochemistry"Organic Letters. 3. 193-196 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Naoki Yamazaki, Masakazu, Atobe, Chihiro Kibayashi: "Nucleophilic Addition of Methyllithium to Chiral Oxime Ethers : Asymmetric Preparation of 1-(Aryl)ethylamines and Application to a Synthesis of Calcimimetics (+)-NPS R-568 and Its Thio Analogue"Tetrahedron Letters. 42. 5029-5032 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Naoki Yamazaki, Masakazu Atobe, Chihiro Kibayashi: "Enantioselective Synthesis of NK-1 Receptor Antagonists (+)-CP-99,994 and (+)-CP-122,721"Tetrahedron Letters. 43. 7979-7982 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Toshimasa Itoh, Naoki Yamazaki, Chihiro Kibayashi: "Asymmetric Synthesis of (-)-Adaline"Organic Letters. 4. 2469-2472 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Naoki Yamazaki, Wataru Dokoshi, Chihiro Kibayashi: "Total Synthesis of (-)-Stellettamide B and Determination of Its Absolute Stereochemistry"Organic Letters, 3. 3. 193-196 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Naoki Yamazaki, Masakazu, Atobe, Chihiro Kibayashi: "Nucleophilic Addition of Methyllithium to Chiral Oxime Ethers: Asymmetric Preparation of 1-(Aryl)ethylamines and Application to a Synthesis of Calcimimetics (+)-NPS R-568 and Its Thio Analogue"Tetrahedron Letters. 42. 5029-5032 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Naoki Yamazaki, Masakazu Atobe, Chihiro Kibayashi: "Enantioselective Synthesis of NK-1 Receptor Antagonists (+)-CP-99,994 and (+)-CP-122,721"Tetrahedron Letters. 43. 7979-7982 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Toshimasa Itoh, Naoki Yamazaki, Chihiro Kibayashi: "Asymmetric Synthesis of (-)-Adaline"Organic Letter. 4. 2459-2472 (2002)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2004-04-14  

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