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A Facile Asymmetric Approach to the Multicyclic Core Structure of Mangicol A
Author(s) -
Ying Jun,
Pu Lin
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404142
Subject(s) - stereoselectivity , chemistry , chemoselectivity , domino , enantiomer , cycloaddition , catalysis , aromatization , enyne , organic chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry
Chiral propargylic ether‐based triene–ynes are synthesized with high enantiomeric purity by employing an asymmetric enyne addition to aldehydes catalyzed by 1,1′‐bi‐2‐naphthol in combination with ZnEt 2 , Ti(O i Pr) 4 and dicyclohexylamine at room temperature. These substrates are found to undergo a one‐pot domino Pauson–Khand and Diels–Alder cycloaddition catalyzed by [RhCl(CO) 2 ] 2 under CO to generate a series of multicyclic products with high chemoselectivity and stereoselectivity. These products contain the multicyclic core structure of mangicol A which could facilitate the synthesis and study of this class of natural products.