Lewis Acid-Promoted Regio- and Diastereoselective Cross-Coupling of Aryl-Substituted 1,2-Diols and Boronic Acids

Abstract

A Lewis acid-promoted highly regio- and diastereoselective C­(sp3)–C­(sp2) cross-coupling reaction between unprotected aryl-substituted 1,2-diols and styryl-, aryl-, heteroaryl-, and polyarylboronic acids has been developed in a one-pot procedure. The regioselective opening of aryl-substituted cyclic boronic esters promoted by a Lewis acid followed by subsequent intramolecular 1,4-transfer of the carbon ligand from boron to a resonance-stabilized benzylic carbenium ion minimizing the allylic 1,3-strain in a stereoselective fashion led to the corresponding α-substituted syn-phenylethyl alcohols. The synthetic utility of the method was illustrated by a short and efficient enantioselective synthesis of cherylline diethyl ether (−)-16.

New Monoterpene-Conjugated Phenolic Constituents from Nutmeg and Their Autophagy Modulating Activities

“…The HMBC correlations from H–OH 13 (δ H 5.87, s) to C-12/C-13/C-14 further confirmed that the monoterpene moiety was linked to C-12. The NOESY correlations (Figure ) of H-30/H-28 and the coupling constant of 6.4 H Z between H-28 and H-29 indicated the relative trans -configuration of C-28 and C-29 in 1 . Thus, the structure of 1 was established and named myrifratin A ( 1 ).…”

“…The NOESY correlations (Figure 2) of H-30/H-28 and the coupling constant of 6.4 H Z between H-28 and H-29 indicated the relative trans-configuration of C-28 and C-29 in 1. 22 Thus, the structure of 1 was established and named myrifratin A (1).…”

Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review

“…Despite the lack of previous records on the biosynthesis of cherylline, it has received much attention with regard to synthetic chemistry aspects and natural product isolation, even until today. 40–42…”

“…Despite the lack of previous records on the biosynthesis of cherylline, it has received much attention with regard to synthetic chemistry aspects and natural product isolation, even until today. [40][41][42] Few studies regarding cherylline have been published since 2017. Shi et al (2018) examined the one-pot synthesis of two constitutional isomers: (±)-latine and (±)-cherylline.…”