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Total synthesis of bafilomycin A(1) relying on iterative 1,2-induction in acyclic precursors

Hanessian, S ; Ma, J ; Wang, W ; Gai, Y

Journal of the American Chemical Society, 2001-10, Vol.123 (42), p.10200-10206 [Periódico revisado por pares]

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Título:
Total synthesis of bafilomycin A(1) relying on iterative 1,2-induction in acyclic precursors
Autor: Hanessian, S ; Ma, J ; Wang, W ; Gai, Y
Assuntos: Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacology ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Macrolides ; Mannitol - chemistry ; Proton-Translocating ATPases - antagonists & inhibitors ; Stereoisomerism ; Valine - chemistry
É parte de: Journal of the American Chemical Society, 2001-10, Vol.123 (42), p.10200-10206
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.
Editor: United States
Idioma: Inglês

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