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Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)‐1,4‐Dideoxymannojirimycin and Further Polyoxygenated 2‐Pyperidones
Author(s) -
Ramírez Elsie,
MezaLeón Rosa L.,
Quintero Leticia,
Höpfl Herbert,
CruzGregorio Silvano,
SartilloPiscil Fernando
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201602048
Subject(s) - chemistry , moiety , enantiopure drug , stereoselectivity , hydrolysis , stereochemistry , wittig reaction , bond cleavage , amine gas treating , oxidative cleavage , derivative (finance) , total synthesis , organic chemistry , catalysis , enantioselective synthesis , financial economics , economics
The total synthesis of (+)‐1,4‐dideoxymannojimycin and the enantiopure synthesis of three polyoxygenated piperidin‐2‐ones from a novel chiron is reported. Starting from 3‐deoxy‐3‐amine‐D‐glucose, by means of the stereoselective aqueous SHOWO protocol (Sequential‐Hydrolysis‐Oxidation‐Wittig Olefination), the unsaturated‐7,3‐lactam‐D‐xylofuranose derivative was prepared, which depending on the oxidative C−C bond cleavage reaction conditions for the furanose moiety, is transformed into either (+)‐1,4‐dideoxymannojirimycin or polyoxygenated piperidin‐2‐ones.