Science of Synthesis

Gilchrist, T. L., Science of Synthesis, (2008) 43, 215.

The most important method for the generation of para-arynes is Bergman cyclization. The prototypical reaction, that of (Z)-hex-3-ene-1,5-diyne (‌193‌), is illustrated in ‌Scheme 82‌. The reaction was first described in detail in 1972,[‌291‌] but it has gained greater recognition and importance since 1987 following the discovery that several natural antibiotics contain the enediyne structural unit. The high activity of these compounds against a variety of cancers is related to their ability to abstract hydrogen atoms from the deoxyribose backbone of DNA, thereby causing cleavage of double-stranded DNA. It is generally assumed that Bergman cyclization precedes hydrogen abstraction in these antibiotics.

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‌Meeeee 88‌ Meeeeeeee Meeeeeeee ee eee Meeeeee Meeeeeeeeee ee 8,8-Meeeeeeeeeeeeeee ee eee Meeeeeee eee Meeeeee ee Meeeeeeee-8,8-eeeee[‌888‌]

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‌Meeeee 88‌ Meeeeeeeeee ee Meeeee Meeeeeeee[‌888‌]

Meeeeeeeee ee eee Meeeeee eeeeeeeeeee ee eee eeeeeeeeee ee eeee-eeeeeeeee eeee eeee eeeeeeeee. Mee eeeeeee, eee eeeeee ‌888‌ eeeeeeeee ee eee eeeeeeee ‌888‌ eeeee eeee eeeeeeeeee (‌Meeeee 88‌). 8,8-Meeeeeeeeeeeeeeeee eee eeeeeee ee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeee, eee eeeee eee eee eeeeeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Me Mee Meeeeeee ee eee Meeeeee Meeeeeeeeee[‌888‌]

References