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A convenient and scalable synthesis of two unusual amino acid units found in dolastatin 16, dolaphenvaline, and dolamethylleuine, is described. Dolastatin 16, which was first isolated from the sea hare Dolabella auricularia by Pettit, exhibits not only strong inhibition of growth for a variety of human cancer cell lines but also potent antifouling activity against the larvae of the barnacle Balanus amphitrite. The key element of the synthesis is an organocatalytic Mannich reaction to construct two contiguous stereocenters in the amino acid units with almost complete enantio- and diastereoselectivity.

Pertenece a

Hokkaido University Collection of Scholarly and Academic Papers  


Umezawa, Taiki -  Sato, Akinori -  Ameda, Yasuto -  Casalme, Loida O. -  Matsuda, Fuyuhiko - 

Id.: 69981611

Idioma: inglés  - 

Versión: 1.0

Estado: Final

Palabras claveDolastatin 16 - 

Tipo de recurso: article (author version)  - 

Tipo de Interactividad: Expositivo

Nivel de Interactividad: muy bajo

Audiencia: Estudiante  -  Profesor  -  Autor  - 

Estructura: Atomic

Coste: no

Copyright: sí

: © 2014 Elsevier Ltd. All rights reserved.

Requerimientos técnicos:  Browser: Any - 

Fecha de contribución: 21-oct-2017


* Tetrahedron letters, 56(1): 168-171

Otros recursos del mismo autor(es)

  1. Total synthesis and biological activity of dolastatin 16 The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Do...
  2. Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls a...
  3. Total synthesis of dolastatin 16 [an abstract of dissertation and a summary of dissertation review]
  4. Total synthesis of dolastatin 16 [an abstract of entire text] この博士論文全文の閲覧方法については、以下のサイトをご参照ください。
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