Tetrahedron p. 10953 - 10970 (1997)
Update date:2022-08-17
Topics:
Fang, Francis G.
Bankston, Donald D.
Huie, Edward M.
Johnson, M. Ross
Kang, Myung-Chol
LeHoullier, Craig S.
Lewis, George C.
Lovelace, Thomas C.
Lowery, Melissa W.
McDougald, Darryl L.
Meerholz, Clive A.
Partridge, John J.
Sharp, Matthew J.
Xie, Shiping
The topoisomerase I inhibitor GI147211C (4) was discovered at Glaxo Wellcome and shown to have promising anti-cancer properties. In order to fully assess the clinical potential of 4, an improved synthesis of the drug substance was required. Herein is described a convergent catalytic asymmetric synthesis of 4 which utilizes as key steps, two Heck reactions, a Sharpless asymmetric dihydroxylation reaction, and a Mitsunobu reaction. A 2-chloroquinoline is shown to be a viable substrate for the final Heck reaction to generate the camptothecin nucleus.
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