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Design of a Functional Chromene‐Type Kobayashi Precursor: Gram‐Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation
Author(s) -
Xu YuanZe,
Sha Feng,
Wu XinYan
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003805
Subject(s) - regioselectivity , aryne , annulation , chemistry , xanthone , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
The 2,2‐dimethyl‐2 H ‐chromene motif is widely found in many bioactive molecules, and is a privileged structure in the pharmaceutical arena. We have developed a concise and regioselective approach to chromenes and chromanes through an aryne‐based synthetic strategy. A practical, gram‐scale synthetic route to a chromene‐type aryne precursor was explored. Subsequently, cyclization under mild conditions afforded tetracyclic xanthone skeletons with excellent regioselectivity. Our approach provides a concise strategy for the gram‐scale synthesis of chromene‐type xanthones such as 6‐deoxyisojacareubin, cylindroxanthone D, staudtiixanthone D, brasilixanthone A and cudracuspixanthone O.