Synthesis and absolute configuration of the first optically active organic molecule with T symmetry: (-)-1,3,5,7-tetrakis3-trishomocubanyl)acetoxy>methyl>adamantane

DOI: 10.1021/jo00314a023

Source and publish data:

Journal of Organic Chemistry p. 106 - 111 (1981)

Update date:2022-08-03

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Authors:

Nakazaki, Masao

Naemura, Koichiro

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Article abstract of DOI:10.1021/jo00314a023

By starting from the Diels-Alder adduct 12 between 2-(methoxycarbonyl)-1,4-benzoquinone (11) and cyclopentadiene, the modified Barborak synthesis of D₃-trishomocubane afforded (-)-2-(1S,3S,5R,6S,8R,10R)-D₃-trishomocubaneacetic acid (19) whose esterification with 1,3,5,7,-tetrakis(hydroxymethyl)adamantane (27) gave (-)-28, the first T symmetric organic molecule with known absolute configuration.

Full text of DOI:10.1021/jo00314a023

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