An Approach to the Total Synthesis of the Marine Ascidian Metabolite Perophoramidine via a Halogen-Selective Tandem Heck/Carbonylation Strategy

A halogen-selective tandem intramolecular Heck/carbonylation reaction has been developed for the construction of the C,E,F-ring system and the C20 quaternary center found in perophoramidine (1). This process can be effected in good yields in the presence of both the chlorine and bromine atoms found in the natural product. In addition, it is possible to introduce the quaternary center at C4 in a stereoselective manner by a lactone enolate alkylation, using NaH and allyl bromide.

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PID https://www.doi.org/10.1021/ol034314d
PID https://www.doi.org/10.1021/ol034314d.s001
URL http://dx.doi.org/10.1021/ol034314d
URL https://pubs.acs.org/doi/abs/10.1021/ol034314d
URL https://academic.microsoft.com/#/detail/2075172366
URL https://pubs.acs.org/doi/pdf/10.1021/ol034314d
URL https://www.ncbi.nlm.nih.gov/pubmed/12713314
URL https://figshare.com/articles/journal_contribution/An_Approach_to_the_Total_Synthesis_of_the_Marine_Ascidian_Metabolite_Perophoramidine_via_a_Halogen-Selective_Tandem_Heck_Carbonylation_Strategy/3746373
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Access Right Open Access
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Author Artman, Gerald D.
Author Weinreb, Steven M.
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Collected From figshare; Datacite; Crossref; Microsoft Academic Graph
Hosted By Organic Letters; figshare
Journal Organic Letters, 5, null
Publication Date 2016-08-20
Publisher American Chemical Society (ACS)
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Source https://science-innovation-policy.openaire.eu/search/publication?articleId=dedup_wf_001::6616846b2ad027002f3bf1eccc47da89
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Last Updated 23 December 2020, 18:04 (CET)
Created 23 December 2020, 18:04 (CET)