Synthesis and absolute configuration of (S)-(-)- and (R)-(+)-2, 3-dihydro-2-(1-methylethenyl)-6-methoxybenzofuran

R Tovar-Miranda; R Cortes-Garcia; LR Trinidad-Nino; P Joseph-Nathan

doi:10.1021/np980521o

Synthesis and absolute configuration of (S)-(-)- and (R)-(+)-2, 3-dihydro-2-(1-methylethenyl)-6-methoxybenzofuran

J Nat Prod. 1999 Aug;62(8):1085-7. doi: 10.1021/np980521o.

Authors

R Tovar-Miranda¹, R Cortes-Garcia, LR Trinidad-Nino, P Joseph-Nathan

Affiliation

¹ Instituto de Ciencias Basicas, Universidad Veracruzana, Apartado Postal 575, Xalapa, Ver., 91000 Mexico, and Departamento de Quimica del Centro de Investigacion y de Estudios Avanzados, Instituto Politecnico Nacional, Apartado 14-7.

PMID: 10479308
DOI: 10.1021/np980521o

Abstract

Resolution of racemic 2,3-dihydro-2-carboxy-6-methoxybenzofuran (2) by recrystallizations of diastereomeric salts prepared with (S)-(-)-alpha-methylbenzylamine and (R)-(+)-alpha-methylbenzylamine gave the starting materials for the four-step total syntheses of (S)-(-)-2,3-dihydro-2-(1-methylethenyl)-6-methoxybenzofuran (1a) and (R)-(+)-2,3-dihydro-2-(1-methylethenyl)-6-methoxybenzofuran (1b). Their absolute configuration was established by chemical correlation.