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Novel One-Pot Total Syntheses of Deoxyvasicinone, Mackinazolinone, Isaindigotone, and Their Derivatives Promoted by Microwave Irradiation

Jifeng LiuArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Ye PingArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Kevin SpragueArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Katie SargentArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Daniel YohannesArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Carmen M. BaldinoArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Christopher J. WilsonArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801Shi‐Chung NgArQule, Inc., 19 Presidential Way, Woburn, Massachusetts 10801
2005en
ABI

Abstract

[reaction: see text]. Total syntheses of deoxyvasicinone (1), mackinazolinone (2), and 8-hydroxydeoxyvasicinone (3) via novel microwave-assisted domino reactions, as well as a novel three-component one-pot total synthesis of isaindigotone (5) promoted by microwave irradiation, are reported. The efficient reaction process enabled us to rapidly access related natural product derivatives and to identify a new class of cytotoxic agents.

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Cited by 80 references