Journal
TETRAHEDRON
Volume 72, Issue 27-28, Pages 4001-4006Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.05.028
Keywords
Tocotrienol; Tocodienol; Oxidative olefin cleavage; C-C coupling; Desulfonylation
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Funding
- National Institute of General Medical Sciences of the National Institutes of Health [P20 GM109005]
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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)-delta-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 delta-tocotrienol as a starting material (24% total yield). The key step in the synthesis is oxidative olefin cleavage of s-tocotrienol to afford the chroman core of 1 with retention of chirality at the C-2 stereocenter. (C) 2016 Elsevier Ltd. All rights reserved.
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