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DOI: 10.1055/s-0041-1737932
Total Synthesis of (+)-Dynemicin A
A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability.
J. Am. Chem. Soc. 1997;
119: 6072-6094
DOI: 10.1021/ja9703741
Key words
(+)-dynemicin - enediyne - Suzuki–Miyaura coupling - Yamaguchi alkynylation - Diels–Alder reaction
Significance
In 1997, Myers and co-workers reported the first total synthesis of (+)-dynemicin A. The potent antitumor antibiotic features a strained 10 membered enediyne motive. Its unique structural characteristics and high reactivity have attracted the interest of the synthetic community since its isolation in the 1980s.
Comment
Ester F was accessed by cross-coupling enol triflate D and arylboronic acid E. The enediyne motive was introduced via Yamaguchi-type acetylide addition onto quinoline G. The Diels–Alder reaction of quinone imine M with isobenzofuran N yielded the natural product after deprotection.
Publication History
Article published online:
18 March 2022
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