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Synthese mittlerer und großer Ringe, XXXIV. Stereoselektive Synthese überbrückter und verzweigter Methyl‐desoxyfuranoside aus 3,6‐Hexanooxepin‐4,5‐dicarbonsäure‐dimethylester
Author(s) -
Tochtermann Werner,
Popp Brigitta,
Mattauch AnneKatrin,
Peters EvaMaria,
Peters Karl,
Schnering Hans Georg Von
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261133
Subject(s) - chemistry , stereoselectivity , stereocenter , stereochemistry , cyclobutene , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis
Syntheses of Medium and Large Rings, XXXIV [1,2] . – Stereoselective Synthesis of Bridged and Branched Methyl Deoxyfuranosides from Dimethyl 3,6‐Hexanooxepine‐4,5‐dicarboxylate The stereoselective synthesis of the bridged methyl furanosides 4–8 with four, five, and six stereogenic centers is described. The reaction sequence starts with the addition of methanol to the oxepine 1 . The photochemical electrocyclic ring closure of 2 gives the cyclobutene 3 . Ruthenium tetraoxide oxidation of 3 leads to the title compound 4 that is further converted to 5–8 by stereoselective reductions.