Total synthesis of the topopyrones: A new class of topoisomerase I poisons

Mark A. Elban; Sidney M. Hecht

doi:10.1021/jo702487r

Total synthesis of the topopyrones: A new class of topoisomerase I poisons

Mark A. Elban, Sidney M. Hecht

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

(Chemical Equation Presented) The topopyrones represent a new class of highly cytotoxic topoisomerase I poisons. Efficient total syntheses of all four naturally occurring members of this class have been accomplished. Key elements of the syntheses include Diels-Alder reactions employing two novel dienes and a titanium-mediated ortho-directed Friedel-Crafts acylation. Additionally, the syntheses of two chlorinated analogues accessible from an advanced intermediate are described.

Original language	English (US)
Pages (from-to)	785-793
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	73
Issue number	3
DOIs	https://doi.org/10.1021/jo702487r
State	Published - Feb 1 2008
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo702487r

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abstract = "(Chemical Equation Presented) The topopyrones represent a new class of highly cytotoxic topoisomerase I poisons. Efficient total syntheses of all four naturally occurring members of this class have been accomplished. Key elements of the syntheses include Diels-Alder reactions employing two novel dienes and a titanium-mediated ortho-directed Friedel-Crafts acylation. Additionally, the syntheses of two chlorinated analogues accessible from an advanced intermediate are described.",

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AB - (Chemical Equation Presented) The topopyrones represent a new class of highly cytotoxic topoisomerase I poisons. Efficient total syntheses of all four naturally occurring members of this class have been accomplished. Key elements of the syntheses include Diels-Alder reactions employing two novel dienes and a titanium-mediated ortho-directed Friedel-Crafts acylation. Additionally, the syntheses of two chlorinated analogues accessible from an advanced intermediate are described.

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Total synthesis of the topopyrones: A new class of topoisomerase I poisons

Abstract

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