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. 2020 Mar 9;59(11):4360-4364.
doi: 10.1002/anie.201915787. Epub 2020 Feb 3.

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594

Tao Xie  1 , Chaoying Zheng  1 , Kuanwei Chen  1 , Haibing He  2 , Shuanhu Gao  1   2
Affiliations

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594

Tao Xie et al. Angew Chem Int Ed Engl. .

Abstract

A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD-594, a complex polycyclic xanthone natural product from Streptomyces sp. TA-0256, in a longest linear sequence (LLS) of 20 steps. The trans-9,10-dihydrophenanthrene-9,10-diol fragment (B-C-D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu-mediated oxidative cyclization. Late-stage stereoselective glycosylation assembled the angular hexacyclic framework with a β-linked 2,6-dideoxy trisaccharide fragment.

Keywords: glycosylation; natural products; oxidative cyclization; total synthesis; xanthones.

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