A Facile Asymmetric Approach to the Multicyclic Core Structure of Mangicol A |
| |
| Authors: | Jun Ying Prof?Dr Lin Pu |
| |
| Affiliation: | Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904‐4319 (USA) |
| |
| Abstract: | 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 ZnEt2, Ti(OiPr)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. |
| |
| Keywords: | asymmetric synthesis Diels– Alder reaction mangicols Pauson– Khand cyclization propargylic alcohols |
|
|
