259267-38-4Relevant articles and documents
Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts
Schmidt, Bernd,Wolf, Felix
, p. 4386 - 4395 (2017/04/28)
The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.
Convenient synthesis of (E)-methyl O-alkylferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza
Mahajan, Rajesh P.,Patil, Shamkant L.,Mali, Raghao S.
, p. 328 - 331 (2007/10/03)
A convenient two step stereoselective synthesis of (E)-methyl O-alkylferulate 5a-c is described from vanillin 1. Reaction of vanillin 1 with allyl-, prenyl- or geranyl- bromide 2a-c has afforded alkyl ethers 3a-c which on reaction with phosphorane 4, under microwave irradiation, gives (E)-methyl O-alkylferulates 5a-c in high yield. In an alternative approach vanillin 1 on reaction with phosphorane 4 provides (E)-methyl ferulate 6 which on reaction with the corresponding bromides 2a-c gives (E)-methyl O-alkylferulates 5a-c.
