CaltechAUTHORS
Published June 19, 2015 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology

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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Supplemental Material - ol5b01292_si_001.pdf

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Additional details

Identifiers

Eprint ID
58230
Resolver ID
CaltechAUTHORS:20150615-081527494

Funding

NSF
1265591
Amgen
Caltech
Drug Research Academy
Danish Cancer Society
NSF Graduate Research Fellowship
DGE-1144469
Arthur R. Adams SURF Endowment
Caltech Summer Undergraduate Research Fellowship (SURF)

Dates

Created
2015-06-15
Created from EPrint's datestamp field
Updated
2021-11-10
Created from EPrint's last_modified field