Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes­: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues

Abstract

The substrate-controlled diastereoselective arylation of chiral aldehydes readily available from carbohydrates is described, using the boron-zinc exchange reaction to generate the transferable aryl groups. The methodology developed was applied to the total synthesis of the styryllactone (+)-7-epi-goniofufurone and analogues thereof.

Total Synthesis of Linear Coumarniolignoids (+) and (−)-Sapiumin C, (−)-Moluccanin, and (−)-Hemidesminine

“…Alternatively, arylation addition reactions of organoboron reagents to aldehydes have become more prevalent using transition-metal catalysts such as Ni (0), − Pd­(II), , Cu­(I/II), − Fe­(III), Ru­(II), , Zn­(II), Ir­(I), Co­(II), and Rh­(I)/(II) complexes. − Among the catalysts, the most heavily studied and robust one was shown to be [Rh­( COD )­Cl 2 ] , as it does not require any additional resources and conditions, such as a microwave, glovebox, additional ligands, anhydrous solvents, and inert atmosphere. Therefore, it was decided to attempt this reaction using a modified Miyaura arylation via [Rh­( COD )­Cl 2 ], ,, involving the addition of an aromatic boronic acid to aldehyde 6 .…”