Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid. uri icon

abstract

  • A new strategy for highly concise, convergent, and enantioselective access to polydeoxypropionates has been developed. ZACA-Pd-catalyzed vinylation was used to prepare smaller deoxypropionate fragments, and then two key sequential Cu-catalyzed stereocontrolled sp(3)-sp(3) cross-coupling reactions allowed convergent assembly of smaller building blocks to build-up long polydeoxypropionate chains with excellent stereoselectivity. We employed this strategy for the synthesis of phthioceranic acid, a key constituent of the cell-wall lipid of Mycobacterium tuberculosis, in just 8 longest linear steps with full stereocontrol.

published proceedings

  • Angew Chem Int Ed Engl

altmetric score

  • 8.874

author list (cited authors)

  • Xu, S., Oda, A., Bobinski, T., Li, H., Matsueda, Y., & Negishi, E.

citation count

  • 25

complete list of authors

  • Xu, Shiqing||Oda, Akimichi||Bobinski, Thomas||Li, Haijun||Matsueda, Yohei||Negishi, Ei-ichi

publication date

  • January 2015

publisher