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Metathesis‐Based De Novo Synthesis of Noviose
Author(s) -
Schmidt Bernd,
Hauke Sylvia
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.201301615
Subject(s) - chemistry , metathesis , ring closing metathesis , salt metathesis reaction , allylic rearrangement , nucleophile , allylic alcohol , stereochemistry , alcohol , total synthesis , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
The rare carbohydrate L ‐(+)‐noviose was synthesized from enantiomerically pure L ‐lactate. The configuration at C‐4 was established by diastereoselective nucleophilic addition to an in‐situ‐generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring‐closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM–allylic‐oxidation sequences.