Total Synthesis and Stereochemistry of Uncialamycin.

Abstract

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Enantioselective synthesis of sealutomicin C

“…Our strategy for the synthesis of sealutomicin C 3 is shown retrosynthetically in Figure 1b. We reasoned that the anthraquinone moiety of sealutomicin C 3 could be installed via a Hauser-Kraus annulation on an iminoquinone formed from oxidation of an alkoxy aniline such as 7, as previously utilized by Nicolaou et al in the syntheses of uncialamycin 5, [10][11][12] leading to a protected triol derivative from which 3 could be formed on global deprotection. The a,b-unsaturated ester functionality in 7 was to be introduced from the terminal alkyne 8, which itself would be derived ultimately from the ketone 9.…”

“…[2][3][4][5][6] AFEs have attracted considerable attention from the synthetic and medicinal chemistry communities owing to their potent antibiotic and antitumor activities, with notable contributions coming from the Myers, Danishefsky, and Nicolaou groups. [7][8][9][10][11][12][13][14] In contrast, sealutomicins B -D 2 -4 all possess a bridging aryl ring in place of the enediyne core, proposed to be formed biosynthetically via Bergman cyclisation of an enediyne precursor, such as sealutomicin A 1. Such reactivity has previously been implicated in the biosynthesis of the natural product unciaphenol 6 from its enediyne precursor uncialamycin 5.…”