Patent ID: 8772484

Claim:
A process for producing a v-coelenteramine compound represented by formula (XIV): (wherein R 1 is hydrogen; a halogen; an aryl which may optionally be substituted with at least one selected from the group consisting of a halogen, hydroxy, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an amino and a dialkylamino having 1 to 6 carbon atoms; an arylalkyl which may optionally be substituted with at least one selected from the group consisting of a halogen, hydroxy, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an amino and a dialkylamino having 1 to 6 carbon atoms; an arylalkenyl which may optionally be substituted with at least one selected from the group consisting of a halogen, hydroxy, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an amino and a dialkylamino having 1 to 6 carbon atoms; an alkyl which may optionally be substituted with an alicyclic group; an alkenyl which may optionally be substituted with an alicyclic group; an alicyclic group, a heterocyclic group; or an alkynyl which may optionally be substituted with an alicyclic group), which comprises: (1) reacting a compound represented by formula (VIII): (wherein R 1 is the same as defined above and R 4 is a protecting group selected from the group consisting of methyl, methoxymethyl, tetrahydropyranyl, benzyl, 4-methoxybenzyl, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, tert-butyldiphenylsilyl and triisopropylsilyl) with a methyltriphenylphosphonium salt in the presence of a solvent and a base to give a compound represented by formula (IX): (wherein R 1 and R 4 are the same as defined above), and, (2) performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by formula (IX) and a compound represented by formula (X) which is prepared by protecting the amino in formula (IX) with R 5 : (wherein R 1 and R 4 are the same as defined above and R 5 is a protecting group selected from the group consisting of acetyl, benzoyl, p-tosyl, tert-butoxycarbonyl and benzyloxycarbonyl) in the presence of a solvent and a catalyst, and then deprotecting R 4 and, if any, R 5 .