Concise Synthesis of Thapsigargin from Nortrilobolide
Research output: Contribution to journal › Journal article › Research › peer-review
Herein, we wish to describe for the first time an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This innovative protocol involves three key steps: a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, a stereoselective α´-acyloxylation in the presence of Mn(OAc)3 and a highly stereoselective reduction of a ketone into its corresponding alcohol highlighting the vital importance of the solvent used during the reaction.
Original language | English |
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Journal | Tetrahedron Letters |
Volume | 56 |
Issue number | 43 |
Pages (from-to) | 5896-5898 |
Number of pages | 3 |
ISSN | 0040-4039 |
DOIs | |
Publication status | Published - 8 Sep 2015 |
- Faculty of Health and Medical Sciences - Thapsigargin, Nortrilobolide, Semissynthesis
Research areas
ID: 143966668