ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Stereoselective total synthesis of (−)-pyrenophorol

Dongamanti Ashok, Sridhar Pervaram, Venkata Ramana Reddy Chittireddy, Sreenivasulu Reddymasu, and Naresh Kumar Vuppula

Osmania University, Hyderabad, India

E-mail: pervaramsridhar@gmail.com

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.

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

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0331-4

Chemical Papers 72 (4) 971–977 (2018)