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Chemical Papers

, Volume 72, Issue 4, pp 971–977 | Cite as

Stereoselective total synthesis of (−)-pyrenophorol

  • Dongamanti Ashok
  • Sridhar Pervaram
  • Venkata Ramana Reddy Chittireddy
  • Sreenivasulu Reddymasu
  • Naresh Kumar Vuppula
Original Paper
  • 72 Downloads

Abstract

A simple and efficient stereoselective synthesis of macrodilactone of (−)-pyrenophorol (1) has been accomplished in 12 steps in 8.3% overall yield, from inexpensive and commercially available (S)-ethyl lactate. This convergent synthesis utilizes an oxidation–reduction protocol and cyclodimerisation under the Mitsunobu reaction conditions as key steps.

Graphical Abstract

Keywords

(S)-ethyl lactate Wittig olefination Intermolecular Mitsunobu cyclization (−)-Pyrenophorol. 

Supplementary material

11696_2017_331_MOESM1_ESM.doc (2.5 mb)
Supplementary material 1 (DOC 2536 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2017

Authors and Affiliations

  • Dongamanti Ashok
    • 1
  • Sridhar Pervaram
    • 1
  • Venkata Ramana Reddy Chittireddy
    • 2
  • Sreenivasulu Reddymasu
    • 3
  • Naresh Kumar Vuppula
    • 4
  1. 1.Department of ChemistryOsmania UniversityHyderabadIndia
  2. 2.Department of ChemistryJawaharlal Nehru Technological UniversityHyderabadIndia
  3. 3.Department of Chemistry, University College of Engineering (Autonomous)Jawaharlal Nehru Technological UniversityKakinadaIndia
  4. 4.Department of ChemistrySri Chaitanya P.G CollegeGodavarikhaniIndia

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