Second Generation Total Synthesis of (–)‐Preussochromone D | Zendy

Kerste Eric | Zendy; Beller Marc Paul | Zendy; Koert Ulrich | Zendy

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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.

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