Abstract
A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).
MeSH terms
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Benzylamines / chemistry
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Benzylamines / metabolism
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Catalysis
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Dihydroxyacetone / chemistry
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Dihydroxyacetone / metabolism
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Fingolimod Hydrochloride
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Hydrogenation
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Immunosuppressive Agents / chemical synthesis*
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Immunosuppressive Agents / metabolism
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Propylene Glycols / chemical synthesis*
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Propylene Glycols / metabolism
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Sphingosine / analogs & derivatives
Substances
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Benzylamines
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Immunosuppressive Agents
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Propylene Glycols
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benzylamine
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Fingolimod Hydrochloride
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Sphingosine
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Dihydroxyacetone