Enantioselective Access to Bicyclo[3.2.1]octadienone Skeleton: Total Syntheses of (+)-Engelharquinone and Its Epoxide

The first enantioselective total syntheses of engelharquinone (2) and its epoxide 3 have been achieved. The key steps include (1) catalytic asymmetric 1,4-addition of a naphthylboronic acid derivative to a masked naphthoquinone derivative by using a chiral Rh-complex and (2) thiolate-promoted stereo...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-03, Vol.19 (6), p.1470-1473
Main Authors: Fukazawa, Takumi, Ando, Yoshio, Ohmori, Ken, Hayashi, Tamio, Suzuki, Keisuke
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first enantioselective total syntheses of engelharquinone (2) and its epoxide 3 have been achieved. The key steps include (1) catalytic asymmetric 1,4-addition of a naphthylboronic acid derivative to a masked naphthoquinone derivative by using a chiral Rh-complex and (2) thiolate-promoted stereospecific construction of the bicyclo­[3.2.1]­octa­dienone scaffold.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00464