A New Artificial Cyclase for Polyprenoids: Enantioselective Total Synthesis of (−)-Chromazonarol, (+)-8-epi-Puupehedione, and (−)-11‘-Deoxytaondiol Methyl Ether
- 18 August 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (36) , 11122-11123
- https://doi.org/10.1021/ja0472026
Abstract
This paper describes a new artificial cyclase, optically pure 3-o-fluorobenzyloxy-2-hydroxy-2‘-(p-methoxybemzyl)-1,1‘-binaphthyl·SnCl4, which is effective for the enantioselective cyclization of 2-(polyprenyl)phenol derivatives to afford polycyclic terpenoids bearing a chroman skeleton such as (−)-chromazonarol, (+)-8-epi-puupehedione, a key synthetic intermediate of (+)-wiedendiol, and (−)-11‘-deoxytaondiol methyl ether.Keywords
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