Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

Dale L. Boger; Christopher W. Boyce; Robert M. Garbaccio; Mark Searcey

doi:10.1016/S0040-4039(98)00232-9

Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

Dale L. Boger, Christopher W. Boyce, Robert M. Garbaccio, Mark Searcey

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

51 Citations (Scopus)

Abstract

The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.

Original language	English
Pages (from-to)	2227-2230
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(98)00232-9
Publication status	Published - 16 Apr 1998
Externally published	Yes

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10.1016/S0040-4039(98)00232-9

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title = "Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride",

abstract = "The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.",

author = "Boger, {Dale L.} and Boyce, {Christopher W.} and Garbaccio, {Robert M.} and Mark Searcey",

note = "Funding Information: important class of agents.” Acknowledgments. We gratefully acknowledge the financial support of the National Institute of Heatlh (CA55276) and the award of an ACS Organic Division Fellowship (RMG) sponsored by Zeneca Pharmaceuticals.",

year = "1998",

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doi = "10.1016/S0040-4039(98)00232-9",

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T1 - Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

AU - Boger, Dale L.

AU - Boyce, Christopher W.

AU - Garbaccio, Robert M.

AU - Searcey, Mark

N1 - Funding Information: important class of agents.” Acknowledgments. We gratefully acknowledge the financial support of the National Institute of Heatlh (CA55276) and the award of an ACS Organic Division Fellowship (RMG) sponsored by Zeneca Pharmaceuticals.

PY - 1998/4/16

Y1 - 1998/4/16

N2 - The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.

AB - The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.

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U2 - 10.1016/S0040-4039(98)00232-9

DO - 10.1016/S0040-4039(98)00232-9

M3 - Article

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VL - 39

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

Abstract

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