An efficient synthesis of (+/-)-trichostatic Acid and analogues: a new route to (+/-)-trichostatin A.
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.
Chatterjee
Anamitra
A
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Indiana 46556, USA.
Richer
Joshua
J
Hulett
Tyler
T
Iska
Vijaya Bhaskara Reddy
VB
Wiest
Olaf
O
Helquist
Paul
P
D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D005231:Fatty Acids, Unsaturated; D006877:Hydroxamic Acids; C066131:trichostatic acid; C012589:trichostatin A