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Total Synthesis of (−)‐ and ent ‐(+)‐Vindorosine: Tandem Intramolecular Diels–Alder/1,3‐Dipolar Cycloaddition of 1,3,4‐Oxadiazoles
Author(s) -
Elliott Gregory I.,
Velcicky Juraj,
Ishikawa Hayato,
Li YongKai,
Boger Dale L.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503024
Subject(s) - intramolecular force , tandem , cycloaddition , stereocenter , chemistry , stereochemistry , computer science , organic chemistry , materials science , composite material , enantioselective synthesis , catalysis
From tandem to pentacycle : The intramolecular tandem [4+2]/[3+2] cycloaddition cascade of 1,3,4‐oxadiazole ( Z )‐ 1 to give the pentacyclic skeleton 2 of (−)‐ and ent ‐(+)‐vindorosine introduces all the requisite substituents and functionality in a single step by which three new rings and four CC bonds form and all six key stereocenters are installed.