Endiyne antibiotic

The anomers 65, containing the intercalator and carbohydrate moieties of the endiyne antibiotic neocarzinostatin, were synthesized from 2-amino-2-deoxy-D-galactose. They were shown to cleave DNA under photoirradiation (365 nm), but with a different site selectivity from that of neocarzinostatin. A multi-gram synthesis of UDP-iV-acetylmuramic acid was made possible by an improved synthesis of the 1-phosphate precursor. ... 

Maretina, LA. and B.A. Trofimov. 2006. Endiyne antibiotics and their models New possibilities of acetylene chemistry. Usp Khim 75 (9) 913-935. 

Figure 1-32. Ring-closure reaction of endiyne anticancer antibiotics.

The endiyne and enyne-allene have attracted the attention, as they undergo facile cycloaromatization to produce reactive biradicals [1], which could mimic the DNA-cleaving mechanism and properties of the new class of very potent antitumor antibiotics calicheamicins [2], esperamicins [3], neocarzinostatin [4], and dynemicins [5]. 

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