| dc.contributor.author | Movassaghi, Mohammad | |
| dc.contributor.author | Piersanti, Giovanni | |
| dc.contributor.author | Piizzi, Grazia | |
| dc.contributor.author | Siegel, Dustin Scott | |
| dc.date.accessioned | 2012-10-05T15:42:49Z | |
| dc.date.available | 2012-10-05T15:42:49Z | |
| dc.date.issued | 2009-11 | |
| dc.date.submitted | 2009-09 | |
| dc.identifier.issn | 0022-3263 | |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.uri | http://hdl.handle.net/1721.1/73652 | |
| dc.description.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). | en_US |
| dc.description.sponsorship | Damon Runyon Cancer Research Foundation (grant no. DRS-39-04) | en_US |
| dc.description.sponsorship | National Institutes of Health (U.S.) and National Institute of General Medical Sciences (U.S.) (grant no. GM074825) | en_US |
| dc.description.sponsorship | Amgen, Inc. | en_US |
| dc.description.sponsorship | AstraZeneca (Firm) | en_US |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society | en_US |
| dc.relation.isversionof | http://dx.doi.org/10.1021/jo901926z | en_US |
| dc.rights | Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. | en_US |
| dc.source | PMC | en_US |
| dc.title | Enantioselective Total Synthesis of (−)-Acylfulvene and (−)- Irofulven | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | Siegel, Dustin S. et al. “Enantioselective Total Synthesis of (−)-Acylfulvene and (−)-Irofulven.” The Journal of Organic Chemistry 74.24 (2009): 9292–9304. | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.contributor.approver | Movassaghi, Mohammad | |
| dc.contributor.mitauthor | Movassaghi, Mohammad | |
| dc.contributor.mitauthor | Piersanti, Giovanni | |
| dc.contributor.mitauthor | Piizzi, Grazia | |
| dc.contributor.mitauthor | Siegel, Dustin Scott | |
| dc.relation.journal | Journal of Organic Chemistry | en_US |
| dc.eprint.version | Author's final manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dspace.orderedauthors | Siegel, Dustin S.; Piizzi, Grazia; Piersanti, Giovanni; Movassaghi, Mohammad | en |
| dc.identifier.orcid | https://orcid.org/0000-0003-3080-1063 | |
| mit.license | PUBLISHER_POLICY | en_US |
| mit.metadata.status | Complete | |
