Premium
A Stereoselective Total Synthesis of Xyolide, a Natural Bioactive Nonenolide
Author(s) -
Maram Lingaiah,
Das Biswanath
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400291
Subject(s) - chemistry , stereoselectivity , total synthesis , intramolecular force , fragment (logic) , mitsunobu reaction , stereochemistry , alcohol , ring closing metathesis , d mannitol , combinatorial chemistry , organic chemistry , mannitol , metathesis , catalysis , polymer , computer science , polymerization , programming language
A stereoselective total synthesis of xyolide, a naturally occurring bioactive nonenolide, has been accomplished. The acid fragment of the molecule has been prepared from D ‐mannitol and the alcohol fragment from (2 Z )‐but‐2‐ene‐1,4‐diol. The synthesis involves the coupling of these two fragments using the Yamaguchi esterification protocol, followed by intramolecular ring‐closing methathesis. The diastereoisomeric alcohol fragment has also been utilized in this synthesis by employing the Mitsunobu esterification.