Development of Antitumor Compounds Using the Chiral Benzaldehyde

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1. Chirai aldol reaction of the chiral benzaldehyde with silyl ketene acetals afforded anti-aldol products with highly stereoselectivity. Thus, chirality of the chiral benzaldehyde was effectively transformed to a chiral carbon chain.2. Aldol reaction of the chiral benzaldehyde with a titanium enolate derived form a thioester gave stereoselectively an anti-aldol product.3. Common synthetic intermediate having four continuous asymmetric carbons was synthesized in highly stereoselective manner and highly optical yield from the chiral benzaldehyde through twice aldol reactions. Total synthesis of styryllactones having a 5-membered lactone, goniofufurone, goniobutenolide A and B was achieved.4. Conversion of a 5-membered lactone to a 6-membered lactone through a lactol was developed. According to this method, styryllactones having a 6-membered lactone, goniodiol, goniotriol, 8-acetylgoniotriol, altholactone, and 9-deoxygoniopypyrone were synthesized.5. Chiral total synthesis of goniofupyrone was succeeded. This synthesis established the structure of goniofupyrone including absolute stereochemistry and revised the previously proposed structure.6. The structure of gonioheptolide A was revised by its synthesis from goniofupyrone. The proposed 8-membered lactone structure was found to be incorrect.7. Amino acid part of AI-77B, an antiulcerogenic antibiotic, and AI-77B analogue were synthesized from the chiral benzaldehyde.8. 1,3-Dipolar cycloaddition of chiral nitrons, derived form the chiral benzaldehyde, with olefins gave stereoselectively cis-3,5-disubstituted isoxazolidines.