Abstract
A group of side chain partially saturated tocotrienol analogues, namely tocoflexols, have been previously designed in an effort to improve the pharmacokinetic properties of tocotrienols. (2R,8′S,3′E)-δ-Tocodienol (1) was predicted to be a high value tocoflexol for further pharmacological evaluation. We now report here an efficient eight-step synthetic route to compound 1 utilizing naturally-occurring δ-tocotrienol as a starting material (24% total yield). The key step in the synthesis is oxidative olefin cleavage of δ-tocotrienol to afford the chroman core of 1 with retention of chirality at the C-2 stereocenter.
Original language | English (US) |
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Pages (from-to) | 4001-4006 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 72 |
Issue number | 27-28 |
DOIs | |
State | Published - 2016 |
Externally published | Yes |
Keywords
- C–C coupling
- Desulfonylation
- Oxidative olefin cleavage
- Tocodienol
- Tocotrienol
ASJC Scopus subject areas
- Drug Discovery
- Biochemistry
- Organic Chemistry