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Synfacts 2022; 18(04): 0354
DOI: 10.1055/s-0041-1737932
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (+)-Dynemicin A

Contributor(s):
Erick M. Carreira
,
Henry Lindner
Myers AG, *, Tom NJ, Fraley ME, Cohen SB, Madar DJ. California Institute of Technology, Pasadena, USA
A Convergent Synthetic Route to (+)-Dynemicin A and Analogs of Wide Structural Variability.

J. Am. Chem. Soc. 1997;
119: 6072-6094
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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.


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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.


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Publication History

Article published online:
18 March 2022

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