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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915787
Subject(s) - xanthone , total synthesis , stereochemistry , chemistry , dihydroxylation , natural product , stereoselectivity , ring (chemistry) , enantioselective synthesis , glycosylation , organic chemistry , biochemistry , catalysis
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.