Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

0479690 - ÚEB 2018 RIV DE eng J - Journal Article
Konrádová, Daniela - Kozubíková, H. - Doležal, Karel - Pospíšil, Jiří
Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol.
European Journal of Organic Chemistry. Roč. 2017, č. 35 (2017), s. 5204-5213. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : Cyclization * Microwave chemistry * Oxygen heterocycles * Synthetic methods * Total synthesis
OECD category: Organic chemistry
Impact factor: 2.882, year: 2017

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.
Permanent Link: http://hdl.handle.net/11104/0275708