Enantioselective Total Synthesis of (−)-Jiadifenolide

Authors

  • Dr. Jing Xu,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358 (USA), Fax: (+1) 858-822-0386
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  • Lynnie Trzoss,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358 (USA), Fax: (+1) 858-822-0386
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  • Weng K. Chang,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358 (USA), Fax: (+1) 858-822-0386
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  • Prof. Dr. Emmanuel A. Theodorakis

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358 (USA), Fax: (+1) 858-822-0386
    • Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358 (USA), Fax: (+1) 858-822-0386
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  • We gratefully acknowledge the National Institutes of Health (NIH) for financial support of this work through Grant Number R01 GM081484-01. We thank the National Science Foundation for instrumentation grants CHE9709183 and CHE0741968. We also thank Dr. Anthony Mrse (UCSD NMR Facility), Dr. Yongxuan Su (UCSD MS Facility), and Dr. Arnold L. Rheingold and Dr. Curtis E. Moore (UCSD X-Ray facility).

Abstract

original image

Neurofunk: Highlights of the synthesis of 1, a potent modulator of neurotrophic factors, include construction of the B ring through an asymmetric Robinson annulation, assembly of the E ring lactone through a novel acid-induced cascade reaction, and Pd0-mediated carbomethoxylation and methylation reactions for the construction of the C and A rings, respectively.

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