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
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.
