A Protecting-Group-Free Synthesis of (−)-Salvinorin A
Research output: Contribution to journal › Research article › Contributed › peer-review
Contributors
Abstract
A concise enantioselective total synthesis of the neoclerodane diterpene (−)-salvinorin A is reported. The stereogenic center at C-12 was installed by catalytic asymmetric propargylation with excellent enantioselectivity, and the remaining six stereogenic centers were set up highly diastereoselectively under substrate control. As for our previous synthesis of racemic salvinorin A, two intramolecular Diels-Alder reactions were applied to generate the tricyclic core. A chemoselective Mitsunobu inversion of a syn 1,2-diol allowed for further streamlining of the original reaction sequence by two steps. Overall, (−)-salvinorin A was synthesized in only 16 steps starting from 3-furaldehyde with 1.4 % total yield. Furthermore, an alternative intramolecular Diels-Alder strategy employing a 2-bromo-1,3-diene moiety was investigated.
Details
Original language | English |
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Pages (from-to) | 7968-7973 |
Number of pages | 6 |
Journal | Chemistry - A European Journal |
Volume | 27 |
Issue number | 29 |
Publication status | Published - 20 May 2021 |
Peer-reviewed | Yes |
External IDs
PubMed | 33784436 |
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Keywords
ASJC Scopus subject areas
Keywords
- Asymmetric catalysis, Cycloaddition, Mitsunobu reaction, Terpenoids, Total synthesis