Abstract: The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R1 is optionally substituted C1-6 alkyl, etc.; W is O, S or NR2; R2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R1 is the same as defined above, and a compound of formula (III) or (IV): wherein R2 is the same as defined above; R3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

Abstract: The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R1 is optionally substituted C1-6 alkyl, etc.; W is O, S or NR2; R2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R1 is the same as defined above, and a compound of formula (III) or (IV): wherein R2 is the same as defined above; R3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

Abstract: The present invention provides a method for easily and inexpensively preparing a racemate or an optically-active 2-(1 -hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione in high yields, 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione which is useful as an intermediate for preparing NFD, and an anticancer agent comprising 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione as an active ingredient. Said 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione is obtained in 4 or 5 steps by using comparatively inexpensive 5 -hydroxynaphthalene-1,4-dione (also referred to as juglone) as a starting material.

Abstract: One of the problems to be resolved by the present invention is to stably and sustainably produce active ingredients contained in Bignoniaceous plants of which a mass production is difficult in a conventional manner. The present invention relates to a method for efficiently preparing an anticancer active ingredient NQ801 by a cell cultivation of Bignoniaceous plants under specific culture conditions. An ingredient-production system in the present invention has an anticancer activity.

Abstract: An object of the present invention is to provide a method for efficiently preparing (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione useful as a medicine at a low cost and in large amounts. According to the present invention, the desired (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione can be prepared with high efficiency at a low cost and in large amounts by asymmetrically reducing 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione in the presence of an asymmetric ruthenium complex and a hydrogen donor.

Abstract: The present invention provides a method for easily and inexpensively preparing a racemate or an optically-active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione in high yields, 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione which is useful as an intermediate for preparing NFD, and an anticancer agent comprising 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione as an active ingredient. Said 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione is obtained in 4 or 5 steps by using comparatively inexpensive 5-hydroxynaphthalene-1,4-dione (also referred to as juglone) as a starting material.

Abstract: An object of the present invention is to provide a method for efficiently preparing (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione useful as a medicine at a low cost and in large amounts. According to the present invention, the desired (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione can be prepared with high efficiency at a low cost and in large amounts by asymmetrically reducing 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione in the presence of an asymmetric ruthenium complex and a hydrogen donor.

Abstract: A novel antitumor compound, 2-(1-hydroxyethyl)-5-hydroxynaphto [2,3-b]furan-4,9-dione, having the following formula is provided.