Protecting‐Group‐Free Diastereoselective Total Synthesis of (±)‐6‐ epi ‐Cleistenolide and Chemoenzymatic Synthesis of (–)‐6‐ epi ‐Cleistenolide | Zendy

Mahajan Pankaj S. | Zendy; Gonnade Rajesh G. | Zendy; Mhaske Santosh B. | Zendy

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Protecting‐Group‐Free Diastereoselective Total Synthesis of (±)‐6‐ epi ‐Cleistenolide and Chemoenzymatic Synthesis of (–)‐6‐ epi ‐Cleistenolide

Author(s) -

Mahajan Pankaj S.,

Gonnade Rajesh G.,

Mhaske Santosh B.

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201403123

Subject(s) - total synthesis , chemistry , hemiacetal , protecting group , stereochemistry , ketone , yield (engineering) , kinetic resolution , diol , enantioselective synthesis , chemical synthesis , aldol reaction , organic chemistry , catalysis , biochemistry , alkyl , materials science , metallurgy , in vitro

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.

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