An efficient synthesis of (+/-)-trichostatic Acid and analogues: a new route to (+/-)-trichostatin A

Organic Letters
Anamitra ChatterjeePaul Helquist

Abstract

An efficient synthesis of rac-trichostatic acid (1) and its analogues is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

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Citations

Jul 8, 2011·Organic Letters·David S Barnett, Scott E Schaus
Dec 4, 2014·Angewandte Chemie·Tao Xu, Xile Hu
Mar 5, 2019·Current Topics in Medicinal Chemistry·Xiaopeng PengJianjun Chen
Aug 21, 2013·The Journal of Organic Chemistry·Matthew N Grayson, Jonathan M Goodman

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