2004 年 62 巻 3 号 p. 184-193
A novel nine-membered enediyne antibiotic N 1999-A 2 was chemically synthesized and its absolute stereochemistry was determined. Chemical evidence of the thiol-triggered activation as well as the DNA cleavage profiles of N 1999-A 2 and its stereoisomers proved that the configuration of the C 11-naphthoate moiety played a dominant role in governing not only the orientation of the thiol attack but also the specificity of DNA cleavage.