Unexpected Syntheses of seco-Cyclopropyltetrahydroquinolines From a Radical 5-Exo-Trig Cyclization Reaction Analogs of CC-1065 and the Duocarmycins 英文参考文献.docVIP

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Unexpected Syntheses of seco-Cyclopropyltetrahydroquinolines From a Radical 5-Exo-Trig Cyclization Reaction Analogs of CC-1065 and the Duocarmycins 英文参考文献.doc

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Unexpected Syntheses of seco-Cyclopropyltetrahydroquinolines From a Radical 5-Exo-Trig Cyclization Reaction Analogs of CC-1065 and the Duocarmycins 英文参考文献

Molecules 2004, 9, 125-133 molecules ISSN 1420-3049 Unexpected Syntheses of seco-Cyclopropyltetrahydroquinolines From a Radical 5-Exo-Trig Cyclization Reaction: Analogs of CC-1065 and the Duocarmycins Hari Pati, Tiffany Howard, Heather Townes, Brian Lingerfelt, LuAnne McNulty and Moses Lee* Department of Chemistry, Furman University, Greenville, SC 29613, USA. *Author to whom correspondence should be addressed: email: moses.lee@ Received: 13 January 2004; in revised form 28 January 2004 / Accepted: 29 January 2004 / Published: 28 February 2004 Abstract: Analogs of the seco-cyclopyrroloindoline (seco-CPI), the DNA alkylation pharmacophore of CC-1065 and the duocarmycins, can be prepared through a 5-exo-trig radical cyclization of a free radical and a 3-chloro-2-allylic moiety. This manuscript reports an unexpected discovery that, depending on the structure and stability of the free radical, the cyclization process leads to the production of an appreciable amount of seco- seco-cyclopropoyltetra- cyclopropyltetrahydroquinolines 7a-d along with the hydroindoline products (6a-e). For instance, free radical reaction of the bromoallylic chloride 5a produced an equal amount of 6-benzyloxy-N-t-butoxycarbonyl-3- (chloromethyl)furano[e]indoline (6a), and 7-benzyloxy-N-t-butoxycarbonyl-3-chloro- 1,2,3,4-tetrahydrofurano[f]quinoline (7a). Three other examples that produced mixtures of indoline and quinoline products are provided. In only one of the examples reported in this manuscript, the 6-benzyloxy-N-t-butoxycarbonyl-3-(chloromethyl)benzo[e]indoline, was a seco-CBI precursor 6e formed exclusively, consistent with literature precedents. Keywords: seco-Cyclopropyltetrahydroquinoline, CC-1065, duocarmycins, (chloromethyl)furano[e]indoline, (chloromethyl)furano[f]tetrahydroquinoline. Molecules 2004, 9 126 Introduction CC-1065 (1) and the duocarmycins [such as duocarmycin SA (2),