Enantioselective Synthesis of (−)‐Halenaquinone |
| |
| Authors: | Subir Goswami Prof. Dr. Kenichi Harada Prof. Dr. Mohamed F. El‐Mansy Dr. Rajinikanth Lingampally Prof. Dr. Rich G. Carter |
| |
| Affiliation: | 1. Department of Chemistry, Oregon State University, Corvallis, OR, USA;2. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan;3. Department of Organometallic and Organometalloid Chemistry, National Research Center, Cairo, Egypt |
| |
| Abstract: | The efficient, 12–14 step (LLS) total synthesis of (?)‐halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide‐catalyzed, Yamada–Otani reaction to establish the C6 all‐carbon quaternary stereocenter, (b) multiple, novel palladium‐mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring. |
| |
| Keywords: | asymmetric synthesis organocatalysis palladium radical reactions total synthesis |
|
|
