Total synthesis of aquatolide
| Authors |
|
|---|---|
| Publication date | 2015 |
| Journal | Organic Letters |
| Volume | Issue number | 17 | 15 |
| Pages (from-to) | 3892-3894 |
| Organisations |
|
| Abstract | A total synthesis of the sesquiterpene lactone aquatolide has been accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition of an allene onto an alpha,beta-unsaturated delta-lactone. Other key steps are an intramolecular Horner-Wadsworth-Emmons reaction to close the lactone and an intramolecular Mukaiyama-type aldol reaction to cyclize the eight-membered ring. Racemic aquatolide has been resolved using preparative HPLC. |
| Document type | Article |
| Note | With supporting information |
| Language | English |
| Published at | https://doi.org/10.1021/acs.orglett.5b01888 |
| Downloads |
500483
(Final published version)
|
| Supplementary materials | |
| Permalink to this page | |