Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues

T A Engler; K O LaTessa; R Iyengar; W Chai; K Agrios

doi:10.1016/0968-0896(96)00192-7

Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues

Bioorg Med Chem. 1996 Oct;4(10):1755-69. doi: 10.1016/0968-0896(96)00192-7.

Authors

T A Engler¹, K O LaTessa, R Iyengar, W Chai, K Agrios

Affiliation

¹ Department of Chemistry, University of Kansas, Lawrence 66045, USA.

PMID: 8931946
DOI: 10.1016/0968-0896(96)00192-7

Abstract

Oxygenated pterocarpans and 5-azapterocarpans are prepared utilizing Lewis acid-promoted reactions of 2-alkoxy-1,4-benzoquinones with 2H-chromenes and N-tosyl-1,2-dihydroquinolines, respectively. Similarly, benzannulated analogues are prepared via reactions of 5-alkoxy-1,4-naphthoquinones with chromenes, and related 2-aryl-2,3-dihydrobenzofurans result from reactions of styrenes with the quinones. Syntheses of 5-thiapterocarpans are also described utilizing Pd(0)-coupling of o-chloromercuriophenols with 2H-chromenes.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anti-HIV Agents / chemical synthesis*
Benzofurans / chemistry*
Benzopyrans / chemistry*
Quinones
Stereoisomerism

Substances

Anti-HIV Agents
Benzofurans
Benzopyrans
Quinones