Pathak, R.B., Dobson, B.C., Ghosh, N. et al. (4 more authors) (2015) Synthesis of the tricyclic core of manzamine A. Organic & Biomolecular Chemistry, 13 (11). 3331 - 3340. ISSN 1477-0520
Abstract
An efficient synthetic approach to the core structure of the manzamine alkaloids is reported, particularly in relation to incorporating a one-carbon unit in ring B from which the aldehyde in ircinal A or the beta-carboline unit in manzamine A could potentially be generated. The key steps involve a Johnson–Claisen rearrangement, enolate alkylation, dithiane alkylation and a stereoselective intramolecular dipolar cycloaddition of an azomethine ylide, which provided the desired tricyclic ABC core structure.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © The Royal Society of Chemistry 2015. This is an author produced version of a paper subsequently published in Organic & Biomolecular Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
|
Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 14 Jul 2015 12:32 |
Last Modified: | 10 Mar 2016 07:04 |
Published Version: | http://dx.doi.org/10.1039/c4ob02582b |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Refereed: | Yes |
Identification Number: | 10.1039/c4ob02582b |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:88027 |