Enantioselective Total Synthesis of (−)-Acylfulvene and (−)- Irofulven
Name
Movassaghi_Enantioselective Total.pdf
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1.29 MB
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Author(s)
Movassaghi, Mohammad
Piersanti, Giovanni
Piizzi, Grazia
Siegel, Dustin Scott
Date Issued
November 2009
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society
Citation
Siegel, Dustin S. et al. “Enantioselective Total Synthesis of (−)-Acylfulvene and (−)-Irofulven.” The Journal of Organic Chemistry 74.24 (2009): 9292–9304.
Version
Author's final manuscript
Abstract
We report our full account of the enantioselective total synthesis of (−)-acylfulvene (1) and (−)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (−)-acylfulvene (1) and (−)-irofulven (2).
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo901926z
