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Capture Compound Mass Spectrometry - A Powerful Tool to Identify Novel c-di-GMP Effector Proteins
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Total synthesis of (-)-bafilomycin A(1).

Karl A Scheidt1, Thomas D Bannister, Akihiro Tasaka

  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Journal of the American Chemical Society
|June 13, 2002
PubMed
Summary

This study details the first highly stereoselective total synthesis of (-)-bafilomycin A(1), a potent vacuolar ATPase inhibitor. Key steps included stereoselective aldol and Suzuki coupling reactions to construct this complex natural product.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Bafilomycin A(1) is a potent inhibitor of vacuolar-type H+-ATPase (V-ATPase).
  • The natural enantiomer, (-)-bafilomycin A(1), presents a significant synthetic challenge due to its complex structure.

Purpose of the Study:

  • To achieve a highly stereoselective total synthesis of (-)-bafilomycin A(1).
  • To develop novel synthetic strategies for constructing complex natural products.

Main Methods:

  • Stereoselective aldol reaction between methyl ketone 8b and aldehyde 60c.
  • Suzuki cross-coupling of advanced intermediates 12 and 39.
  • Diastereoselective double asymmetric crotylboration reactions for stereocenter installation.
  • Macrolactonization to form the final ring structure.
  • Mukaiyama aldol reaction and final deprotection using TAS-F.

Main Results:

  • Successful construction of (-)-bafilomycin A(1) with high stereoselectivity.
  • Efficient synthesis of key fragments 12 and 39 through multi-step sequences.
  • Demonstration of the utility of stereoselective aldol and Suzuki coupling reactions in complex molecule synthesis.

Conclusions:

  • The described synthetic route provides a reliable method for accessing (-)-bafilomycin A(1).
  • The study highlights the importance of strategic bond formations and stereochemical control in total synthesis.
  • This work contributes to the broader understanding of V-ATPase inhibition and potential therapeutic applications.