We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Protecting-Group-Free Diastereoselective Total Synthesis of (±)-6- epi-Cleistenolide and Chemoenzymatic Synthesis of (-)-6- epi-Cleistenolide.
- Authors
Mahajan, Pankaj S.; Gonnade, Rajesh G.; Mhaske, Santosh B.
- Abstract
A short, efficient, practical, and protecting-group-free diastereoselective total synthesis of (±)-6- epi-cleistenolide ( 1) has been achieved in five steps in 60 % overall yield. The use of a chemoenzymatic approach also gave (-)-6- epi-cleistenolide ( 1) (>99.9 % ee). The Achmatowicz reaction, chemoselective oxidation of a hemiacetal, diastereoselective 1,3- anti reduction of a β-hydroxy ketone, and enzymatic resolution of a 1,3-diol are the key features of this linear total synthesis. The synthetic strategy demonstrated in this paper could be extended for an asymmetric total synthesis of (-)-cleistenolide ( 1) and related biologically active natural products.
- Subjects
ASYMMETRIC synthesis; LIPASES; HETEROCYCLIC compounds; ENZYMATIC analysis; OXYGEN; ORGANIC chemistry
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 36, p8049
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403123