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A stepwise lactol carbocyclisation to bridged ethers via a keto–acetal cascade
| Content Provider | SAGE Publishing |
|---|---|
| Author | McCarthy, Sean Marson, Charles M. |
| Copyright Year | 2022 |
| Abstract | Lactol carbocyclisations provide a succinct method of constructing the oxabicyclo[3.2.1]octane scaffold, a motif present in various natural products of medicinal interest. Lactols containing an unsaturated ketone or ester were prepared by olefin cross-metathesis; an electrophilic alkene derived from methyl vinyl ketone underwent concomitant terminal α-methylenation and oxa-Michael addition to give a bridged lactol which then underwent oxygen-to-carbon transposition in the presence of titanium (IV) chloride giving the desired unsaturated carbocyclic seven-membered bridged ether via a novel dehydrative cascade considered to involve titanium enolates. |
| Related Links | https://journals.sagepub.com/doi/pdf/10.1177/17475198221079498?download=true |
| ISSN | 17475198 |
| Issue Number | 1 |
| Volume Number | 46 |
| Journal | Journal of Chemical Research (CHL) |
| e-ISSN | 20476507 |
| DOI | 10.1177/17475198221079498 |
| Language | English |
| Publisher | Sage Publications UK |
| Publisher Date | 2022-02-27 |
| Publisher Place | London |
| Access Restriction | Open |
| Rights Holder | © The Author(s) 2022 |
| Subject Keyword | oxa-Michael acetal formation enone–lactol cyclisation keto–acetal cascade dehydrative rearrangement bridged ether synthesis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry |
