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Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

preprint
revised on 24.03.2020 and posted on 24.03.2020 by Takayuki Tonoi, Miyuki Ikeda, Teruyuki Sato, Takehiko Inohana, Ryo Kawahara, Takatsugu Murata, Isamu Shiina
An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.

History

Email Address of Submitting Author

shiina@rs.kagu.tus.ac.jp

Institution

Tokyo University of Science

Country

Japan

ORCID For Submitting Author

0000-0002-8749-2540

Declaration of Conflict of Interest

No conflict of interest

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