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An Expeditious Assembly of 3,4‐Benzannulated 8‐Oxabicyclo[3.2.1]octane Systems by [2+2+2] Alkyne Cyclotrimerisation: Total Synthesis of (–)‐Bruguierol A (Eur. J. Org. Chem. 33/2007)
Author(s) -
Ramana Chepuri V.,
Salian Sumanth R.,
Gonnade Rajesh G.
Publication year - 2007
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.200790088
Subject(s) - alkyne , chemistry , octane , bicyclic molecule , total synthesis , cover (algebra) , stereochemistry , catalysis , organic chemistry , mechanical engineering , engineering
The cover picture shows the use of a [2+2+2] cyclotrimerization reaction for the construction of strained benzannulated 8‐oxabicyclo[3.2.1]octane systems. Wilkinson's catalyst was found to be successful in accomplishing this cross alkyne cyclotrimerization for oxa‐bridged bicyclic systems. The first total synthesis of (–)‐bruguierol A, that establishes its absolute configuration, was accomplished by employing this approach. Details are discussed in the Short Communication by C. V. Ramana et al. on p. 5483 ff.