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Second Generation Total Synthesis of (–)‐Preussochromone D
Author(s) -
Kerste Eric,
Beller Marc Paul,
Koert Ulrich
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000465
Subject(s) - stereocenter , chemistry , enantioselective synthesis , total synthesis , yield (engineering) , stereoselectivity , natural product , stereochemistry , ring (chemistry) , michael reaction , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
An improved enantioselective synthesis of the natural product (–)‐preussochromone D ( 3 ) and first insights into a possible route to the trans ‐preussochromones E and F are described. Starting from commercially available 5‐hydroxy‐4 H ‐chromen‐4‐one, two stereocenters are established via auxiliary controlled Michael addition in excellent yield and stereoselectivity. Subsequent build‐up of the five‐membered ring gave access to (–)‐preussochromone D in an improved overall yield and less synthetic steps than previously reported. The total syntheses of preussochromones E and F on a related route were also investigated and first findings are reported herein.