New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E).

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,11′E)-δ-Tocodienol (1) was predicted to be a high value tocoflexol for further pharmacological evaluation. We now report here an efficient 8-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.

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Synthesis of (2 R ,8′ S ,3′ E )-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol

Liu

Satheesh

Zhang

et al. 2016

Tetrahedron

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New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E).

Cited by 1 publication

References 7 publications

Synthesis of (2 R ,8′ S ,3′ E )-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol

Synthesis of (2 R ,8′ S ,3′ E )-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol

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