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Microwave‐Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol
Author(s) -
Konrádová Daniela,
Kozubíková Hana,
Doležal Karel,
Pospíšil Jiří
Publication year - 2017
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.201701021
Subject(s) - chemistry , coumarin , cinnamic acid , regioselectivity , synthon , total synthesis , claisen rearrangement , derivative (finance) , phenol , aldehyde , natural product , organic chemistry , protecting group , combinatorial chemistry , financial economics , economics , catalysis , alkyl
Herein we describe a one‐pot microwave‐assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.