Enantioselective Total Synthesis of (−)-Acylfulvene and (−)- Irofulven
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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).
Date issued
2009-11Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
0022-3263
1520-6904