Reinvestigating Tatanans A–C

  • Author: Vikki Cantrill
  • Published: 07 April 2013
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Nature Chemistry/Nature Publishing Group
thumbnail image: Reinvestigating Tatanans A–C

A class of complex polyphenolic natural products was previously reported to be potent antidiabetic agents. A synthetic route to these compounds, tatanans A, B, and C, could prompt effective new treatments for diabetes if proven.

The total synthesis of tatanan A (pictured), which has three consecutive tertiary stereocenters, was achieved in 13 steps with a series of sequential [3,3]-sigmatropic rearrangements in 13 % yield by Brian Miller, Armen Zakarian, and colleagues from the University of California, Santa Barbara, and Florida State University, both USA. Tatanans B and C were obtained in 12 steps, including an aromatic group differentiation step, in 4 and 8 % yields, respectively.

Disappointingly, this study showed tatanans A–C had no antidiabetic activity. The origin of the discrepancy is unclear, but perhaps another natural product responsible for the biological effects was co-isolated during the original study.

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