Chemical synthesis and optical purity determination of optically active 1,2-epoxyindan and alcohol products which are also derived from mammalian or microbial metabolism of indene or indanones

Abstract

(+)-trans-2-Bromo-1-hydroxyindan (5) has been resolved into itsenantiomersby preparative h.p.l.c. orfractional crystallization of the bromo-menthyloxy-acetoxydiastereoisomers (6a) and (6b). The bromohydrin (5) or bromo-esters (6a, 6b, and 7) have in turn been converted into (–)-(1R,2S)-1,2-epoxyindan (2), (–)(1R,2R)-trans-1-acetoxy-2-bromoindan (7), (+)-(1S)-indanol (8), (–)-(1R,2R)-trans-indan-1,2-diol (3), and (–)-(1S,2R)-cis-indan-1,2-diol (4). The optical purity of the alcohol products (3), (4), and (8) was determined by n.m.r. and h.p.l.c. analysis of their 2-methoxy-2-phenyl-2-trifluoromethylacetates. The previously unknown optical purity of the chiral alcohols (3), (4), (5), and (8), which had been isolated in earlier mammalian and microbial metabolism studies, has also been deduced.