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Studies on the synthesis of bafilomycin A(1): stereochemical aspects of the fragment assembly aldol reaction for construction of the C(13)-C25) segment

Academic Article
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Overview

authors

  • Roush, William
  • Bannister, Thomas
  • Wendt, M. D.
  • Jablonowski, J. A.
  • Scheidt, K. A.

publication date

  • June 2002

journal

  • Journal of Organic Chemistry  Journal

abstract

  • Highly stereoselective syntheses of aldols 8a-c corresponding to the C(13)-C(25) segment of bafilomycin A(1) were developed by routes involving fragment assembly aldol reactions of chiral aldehyde 6a and the chiral methyl ketones 7. A remote chelation effect plays a critical role in determining the stereoselectivity of the key aldol coupling of 6a and the lithium enolate of 7b. The protecting group for C(23)-OH of the chiral aldehyde fragment also influences the selectivity of the lithium enolate aldol reaction. In contrast, the aldol reaction of 6a and the chlorotitanium enolates of 7a,c were much less sensitive to the nature of the C(15)-hydroxyl protecting group. Studies of the reactions of chiral aldehydes with Takai's (gamma-methoxyallyl)chromium reagent 40 are also described. The stereoselectivity of these reactions is also highly dependent on the protecting groups and stereochemistry of the chiral aldehyde substrates.

subject areas

  • Aldehydes
  • Anti-Bacterial Agents
  • Catalysis
  • Crystallography, X-Ray
  • Lithium Compounds
  • Macrolides
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo016413f

PubMed ID

  • 12054963
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Additional Document Info

start page

  • 4275

end page

  • 4283

volume

  • 67

issue

  • 12

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