A series of naphthoquinones based on the naphtho [2, 3-b] furan-4, 9-dione skeleton such as (−)-5-hydroxy-2-(1′-hydoxyethyl) naphtho [2, 3-b] furan-4, 9-dione (1) and its positional isomer,(−)-8-hydroxy-2-(1′-hydoxyethyl) naphtho [2, 3-b] furan-4, 9-dione (2), which are secondary metabolites found in the inner bark of Tabebuia avellanedae, were stereoselectively synthesized and their biological activities were evaluated in conjunction ...