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Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594
Author(s) -
Xie Tao,
Zheng Chaoying,
Chen Kuanwei,
He Haibing,
Gao Shuanhu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915787
Subject(s) - xanthone , total synthesis , chemistry , stereochemistry , dihydroxylation , stereoselectivity , natural product , ring (chemistry) , enantioselective synthesis , glycosylation , diol , organic chemistry , catalysis , biochemistry
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.