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Stereoselective total synthesis of (−)-(5S,8R,13S,16R)-pyrenophorol

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Abstract

The total synthesis of 16-membered C 2-symmetric dilactone (−)-(5S,8R,13S,16R)-pyrenophorol was accomplished starting from enantiomerically pure propylene oxide prepared by hydrolytic kinetic resolution of (±)-propylene oxide with key steps of cross-metathesis and intermolecular Mitsunobu cyclization for the construction of macrolactone.

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Acknowledgments

We are grateful to CSIR-IICT, Hyderabad for providing analytical facilities.

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Authors and Affiliations

  1. Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar, 522510, Andhra Pradesh, India

    Perugu Edukondalu, Reddymasu Sreenivasulu & Rudraraju Ramesh Raju

  2. Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500 007, India

    Barreddi Chiranjeevi

  3. Department of Chemistry, Sri Chaitanya P.G. College, Godavarikhani, 505 209, India

    Vuppula Naresh Kumar

Authors
  1. Perugu Edukondalu
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  2. Reddymasu Sreenivasulu
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  3. Barreddi Chiranjeevi
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  4. Vuppula Naresh Kumar
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  5. Rudraraju Ramesh Raju
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Correspondence to Barreddi Chiranjeevi, Vuppula Naresh Kumar or Rudraraju Ramesh Raju.

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Edukondalu, P., Sreenivasulu, R., Chiranjeevi, B. et al. Stereoselective total synthesis of (−)-(5S,8R,13S,16R)-pyrenophorol. Monatsh Chem 146, 1309–1314 (2015). https://doi.org/10.1007/s00706-014-1406-3

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  • DOI: https://doi.org/10.1007/s00706-014-1406-3

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