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HERO ID
7952352
Reference Type
Journal Article
Title
Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone
Author(s)
Smi, N; Ainali, NM; Agapiou, E; Papadopoulos, L; Papageorgiou, GZ; Bikiaris, DN; Pandey, G; Fernandes, R; Dey, D; Majumder, B
Year
2018
Is Peer Reviewed?
1
Journal
Tetrahedron
ISSN:
0040-4020
Volume
74
Issue
39
Page Numbers
5752-5757
Language
English
DOI
10.1016/j.tet.2018.08.016
Web of Science Id
WOS:000444664000020
Abstract
A concise asymmetric total synthesis of Amaryllidaceae alkaloid (+)-trans-dihydronarciclasine is accomplished starting from optically pure 7-azabicyclo[2.2.1]heptanone scaffold in 13 linear steps. Key features of the strategy include substrate-directed stereoselective installation of the trans B-C ring junction and regioselective Wacker-type internal olefin oxidation to provide a rapid access to all hydroxyl functionalities over the key cyclohexane ring in a stereocontrolled manner. 2018 Elsevier Ltd
Keywords
Amaryllidaceae alkaloids; (+)-trans-dihydronarciclasine; 7-Deoxy-pancrastatin; Trans-B-C ring junction stereochemistry; Wacker-type internal olefin oxidation
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