Total Synthesis of (+)-Omphadiol

Authors

  • Gang Liu,

    1. Department of Chemistry, Texas A&M University, P. O. Box 30012, College Station, TX 77842 (USA)
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  • Prof. Dr. Daniel Romo

    Corresponding author
    1. Department of Chemistry, Texas A&M University, P. O. Box 30012, College Station, TX 77842 (USA)
    • Department of Chemistry, Texas A&M University, P. O. Box 30012, College Station, TX 77842 (USA)
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  • The work was supported by the Welch Foundation (A-1280) and NSF (CHE-0809747, partial). We thank Morgan Shirley for technical assistance and Mikail Abbasov for performing calculations and creating the graphic for the cover of this Issue. We thank Prof. Zheng and Prof. Shen for providing the spectroscopic data of natural omphadiol.

Abstract

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A smooth transition from (R)-carvone to a β-lactone and then to (+)-omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 % overall yield. All six contiguous stereogenic centers were introduced in a highly diastereoselective manner. Key steps include a nucleophile-promoted aldol lactonization, a single-pot, sequential intra-/intermolecular dialkylation, a tandem olefin isomerization/RCM, and a cyclopropanation with unusual facial selectivity.

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