Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues.
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.
Engler
T A
TA
Department of Chemistry, University of Kansas, Lawrence 66045, USA.
LaTessa
K O
KO
Iyengar
R
R
Chai
W
W
Agrios
K
K
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D001572:Benzofurans / Q000737:chemistry*; D001578:Benzopyrans / Q000737:chemistry*; D011809:Quinones; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D001572:Benzofurans; D001578:Benzopyrans; D011809:Quinones