The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

Yuuki Takada, Masahiro Umehara, Ryosuke Katsumata, Yoichi Nakao, Junji Kimura

研究成果: Article査読

14 被引用数 (Scopus)

抄録

We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-l-Ala, 24-d-MePhe, 37-l-Ile, 43-d-Ala, 15-d-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure-activity relationships of kulokekahilide-2 and its analogs indicate the importance of an l-amino acid at position 21.

本文言語English
ページ(範囲)659-669
ページ数11
ジャーナルTetrahedron
68
2
DOI
出版ステータスPublished - 2012 1 14

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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