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CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1139-1156
DOI: 10.1055/s-0037-1611654
DOI: 10.1055/s-0037-1611654
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General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual SNAr Cyclizations of Aryl Fluorides
This work was supported by JSPS KAKENHI Grant Numbers JP16H06351, JP16H01137, JP16H04107, JP18H04391 and Nagase Science and Technology Foundation.Weitere Informationen
Publikationsverlauf
Received: 13. Dezember 2018
Accepted: 17. Dezember 2018
Publikationsdatum:
23. Januar 2019 (online)
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Dedicated to the memory of the late Professor Sho Ito
Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
Abstract
A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) SNAr oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (–)-rotenone and (–)-deguelin, was prepared from d-araboascorbic acid in five steps. Also described is the conversion of (–)-deguelin into oxidized congeners, (–)-tephrosin and (+)-12a-epi-tephrosin.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611654.
- Supporting Information
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