Protecting‐Group‐Free Diastereoselective Total Synthesis of (±)‐6‐epi‐Cleistenolide and Chemoenzymatic Synthesis of (–)‐6‐epi‐Cleistenolide. Issue 36 (31st October 2014)

• Record Type: Journal Article
• Authors: Mahajan, Pankaj S.; Gonnade, Rajesh G.; Mhaske, Santosh B.
• Is Part Of: European journal of inorganic chemistry. Issue 36(2014)
• Page Start: 8049
• Page End: 8054
• Publication Date: 2014-10-31
• Subjects: Total synthesis -- Asymmetric synthesis -- Diastereoselectivity -- Lipases -- Oxygen heterocycles -- Enzyme catalysis; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201403123
• Languages: English
• ISSNs: 1434-1948

Abstract

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. 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 ) with >99.9 % ee .