Synthesis and absolute configuration of the first optically active organic molecule with T symmetry; (–)-1,3,5,7-tetrakis[2-(1S,3S,5R,6S,8R,10R)-D3-trishomocubanylacetoxymethyl]adamantane

Abstract

Starting from the Diels–Alder adduct (3) between 2-methoxycarbonyl-1,4-benzoquinone and cyclopentadiene, a modified Barborak's synthesis of D₃-trishomocubane afforded (–)-2-(1S,3S,5R,6S,8R,10R)-D₃-trishomocubaneacetic acid (11) whose esterification with 1,3,5,7-tetrakis(hydroxymethyl)adamantane (1) gave (–)-(2), the first organic molecule of T symmetry with known absolute configuration.