Yadav, Jhillu Singh ; Singh, Shweta ; Das, Saibal (2017) An Enantioselective Approach to Pinguisane Sesquiterpenes: Total Synthesis of (-)-Pinguisenol and (-)-Isonaviculol European Journal of Organic Chemistry, 2017 (19). pp. 2824-2830. ISSN 1434-193X
Full text not available from this repository.
Official URL: http://doi.org/10.1002/Ejoc.201700395
Related URL: http://dx.doi.org/10.1002/Ejoc.201700395
Abstract
A short and efficient enantioselective approach to pinguisane-type sesquiterpenes has been developed starting from a Hajos–Parrish-type ketone. This led to the first total syntheses of isonaviculol (10 steps, 6.6 % overall yield) and natural pinguisenol (9 steps, 12 % overall yield). The key reactions were regioselective thioketal protection, stereoselective cyclopropanation using Furukawa's protocol, diastereoselective hydrogenation of an olefin using a Thalesnano H-Cube Pro flow reactor, Li/liquid NH3 mediated cyclopropane reduction, and a PCC-mediated 1,3-oxidative transposition sequence.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley & Sons, Inc. |
| ID Code: | 135694 |
| Deposited On: | 10 Aug 2023 08:18 |
| Last Modified: | 10 Aug 2023 08:18 |
Repository Staff Only: item control page
