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- Title
Nitromethane as a Carbanion Source for Domino Benzoannulation with Ynones: One‐Pot Synthesis of Polyfunctional Naphthalenes and a Total Synthesis of Macarpine.
- Authors
Singh, Shweta; Samineni, Ramesh; Pabbaraja, Srihari; Mehta, Goverdhan
- Abstract
A one‐pot, transition‐metal‐free, domino Michael/SNAr protocol of general applicability has been devised for the regioselective synthesis of polyfunctional naphthalenes by employing nitromethane and ortho‐haloaryl ynones. Utilization of nitromethane as a one carbon carbanion source that is incorporated into a variety of ynones, ends up as an aromatic nitro substituent. The application of this domino process towards a total synthesis of the polycyclic alkaloid macarpine demonstrate for the efficacy of this methodology. The conceptually simple approach to affect regioselective, multifunctional benzoannulation of ynones displays wide substrate scope and functional‐group tolerance and has been implemented with substituted nitromethanes, as well as with alicyclic o‐haloynones.
- Subjects
NITROMETHANE; CARBANIONS; ANNULATION; NAPHTHALENE; FUNCTIONAL groups
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 51, p17089
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201810652