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A Symmetry‐Based Approach to the Heterobicyclic Core of the Zaragozic Acids – Model Studies in the Pseudo C 2 ‐Symmetric Series
Author(s) -
Wang Yuzhou,
Gang Sylvia,
Bierstedt Anja,
Gruner Margit,
Fröhlich Roland,
Metz Peter
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700122
Subject(s) - chemistry , stereocenter , hydrogenolysis , octane , series (stratigraphy) , intramolecular force , derivative (finance) , acetic acid , symmetry (geometry) , ether , acetal , core (optical fiber) , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , computer science , mathematics , paleontology , telecommunications , geometry , financial economics , economics , biology
Using a two‐directional strategy, a concise synthesis of a pseudo C 2 ‐symmetric tetrabenzyl ether of a hexaol diketone was accomplished. Hydrogenolysis of this compound in the presence of acetic acid and subsequent peracetylation triggered a group‐selective intramolecular acetalization to give the desired 2,8‐dioxabicyclo[3.2.1]octane derivative with correct relative and absolute configurations at all stereogenic centers of the heterobicyclic core.