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Published June 19, 2015 | public
Journal Article Open

Exceedingly Efficient Synthesis of (±)-Grandifloracin and Acylated Analogues

Abstract

A highly efficient regio- and stereoselective total synthesis of (±)-grandifloracin via a tandem dearomative epoxidation/spontaneous Diels–Alder cyclodimerization from salicylic acid in only four steps is reported. The synthetic route allows for late-stage diversification of the core structure to give ready access to analogues of this promising agent against pancreatic cancer.

Additional Information

© 2015 American Chemical Society. Received: May 1, 2015. Publication Date (Web): June 10, 2015. The authors wish to thank NSF (1265591), Amgen, and Caltech for financial support. M.B. thanks the Drug Research Academy and the Danish Cancer Society for financial support. D.C.D. (Caltech) thanks the National Science Foundation for financial support (Predoctoral Research Fellowship, No. DGE-1144469). L.C. (Caltech) is grateful to the Arthur R. Adams SURF Endowment. The Caltech Center for Catalysis and Chemical Synthesis (C3S) and especially Dr. Scott Virgil (Caltech) are acknowledged for help with chiral separation. Dr. Michael K. Takase (Caltech) is acknowledged for X-ray crystallographic structural determination.

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