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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 16
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Original Articles

Alternate Synthesis of HSP90 Inhibitor AT13387

Cuirong Liang School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu, China
,
Lingling Gu School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu, China
,
Yang Yang School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, China
&
Xin Chen School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu, ChinaCorrespondence[email protected]
Pages 2416-2425 | Received 09 Jan 2014, Published online: 01 Jul 2014
 
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Abstract

AT13387 is a novel HSP90 inhibitor, and it is currently used in clinical trials for the treatment of refractory gastrointestinal stromal tumors (GIST). In this article, two synthetic routes are described for synthesizing the title compound via [2 + 2 + 2] cycloaddition of dipropargylamine derivatives and propargyl alcohol as a key step. The alternate synthetic methods are economical and suitable for multigram-scale preparation of AT13387 and the related isoindoline derivatives.

GRAPHICAL ABSTRACT

Notes

a Catalyst: Cp*RuCl(PPh3)2 = pentamethylcyclopenta-dienylbis-(triphenylphosphine)ruthenium(II) chloride; CpRuCl(PPh3)2 = cyclopentadienylbis-(triphenylphosphine)ruthenium(II) chloride; (PPh3)3RhCl = tris(triphenylphosphine)rhodium(I) chloride.

b NR, no reaction.

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