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Synthesis 2017; 49(08): 1816-1833
DOI: 10.1055/s-0036-1588925
DOI: 10.1055/s-0036-1588925
paper
Sequential Tandem Transformations of Functionalized Diazanorbornenes: Facile Strategy towards Pentacyclic Frameworks with Multiple Stereocenters
Further Information
Publication History
Received: 31 October 2016
Accepted after revision: 01 December 2016
Publication Date:
30 December 2016 (online)
Abstract
The design, synthesis, and comprehensive utilization of diazanorbornene systems incorporating a flexible hydroxy group are described. The Lewis acid catalyzed intramolecular rearrangement of these strained alkenes gave cyclopentannulated dihydro-2H-pyrans, whereas the intermolecular sequential Lewis acid/palladium-mediated reaction with o-iodoanilines gave pentacyclic frameworks through multiple bond formation (C–C, C–N, C–O).
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588925.
- Supporting Information
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