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

Anamitra Chatterjee; Joshua Richer; Tyler Hulett; Vijaya Bhaskara Reddy Iska; Olaf Wiest; Paul Helquist

doi:10.1021/ol9029116

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

Org Lett. 2010 Feb 19;12(4):832-4. doi: 10.1021/ol9029116.

Authors

Anamitra Chatterjee¹, Joshua Richer, Tyler Hulett, Vijaya Bhaskara Reddy Iska, Olaf Wiest, Paul Helquist

Affiliation

¹ Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Indiana 46556, USA.

PMID: 20104892
DOI: 10.1021/ol9029116

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Fatty Acids, Unsaturated / chemical synthesis*
Fatty Acids, Unsaturated / chemistry
Hydroxamic Acids / chemical synthesis*
Hydroxamic Acids / chemistry
Molecular Structure
Stereoisomerism
Streptomyces / chemistry

Substances

Fatty Acids, Unsaturated
Hydroxamic Acids
trichostatic acid
trichostatin A