A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction.
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).
Sugiyama
Shigeo
S
Meiji Pharmaceutical University, Tokyo, Japan.
Arai
Satoshi
S
Kiriyama
Matsuri
M
Ishii
Keitaro
K
D001596:Benzylamines / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D004098:Dihydroxyacetone / Q000737:chemistry / Q000378:metabolism; D000068876:Fingolimod Hydrochloride; D006865:Hydrogenation; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000378:metabolism; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000378:metabolism; D013110:Sphingosine / Q000031:analogs & derivatives
D001596:Benzylamines; D007166:Immunosuppressive Agents; D011409:Propylene Glycols; C030796:benzylamine; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine; D004098:Dihydroxyacetone