Open AccessA formal synthesis of (+)-muricatacin from D-xylose
Author(s) -
J Velimir Popsavin,
Sanja Grabež,
N Ivana Krstic,
Mirjana Popsavin,
Dejan Djoković
Publication year - 2003
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc0311795p
Subject(s) - wittig reaction , lactol , stereospecificity , xylose , chemistry , formal synthesis , lactone , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , fermentation
A multistep route towards the aldehydo-lactone 19, the final chiral precursor in a new stereospecific synthesis of (+)-muricatacin, has been developed starting from D-xylose. The key step of the synthesis involves an E-selective Wittig olefination of the lactol 6 with methoxycarbonylmethylidene triphenylphosphorane, followed by successive catalytic reduction and ?-lactonisation processes. Subsequent selective functional groups interconver- sions furnished the key six-carbon intermediate 19, which can be converted into the (+)-muricatacin via a three-step sequence already described in the chemical literature.