Tetrahedron

Synthesis of (+)-1, 3, 5, 7-tetrakis [2-(1S, 3S, 5R, 6S, 8R, 10R)-D 3-trishomocubanylbuta-1, 3-diynyl] adamantane: The first optically active organic molecule with t …

K Naemura, Y Hokura, M Nakazaki

Index: Naemura, Koichiro; Hokura,Yukio; Nakazaki, Masao Tetrahedron, 1986 , vol. 42, # 6 p. 1763 - 1768

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Citation Number: 15

Abstract

(-)-(1S, 3S, 5R, 6S, 8R, 10R)-Trishomocubanethanoic acid (5) of known absolute configuration and absolute rotation was converted into (+)-(1S, 3S, 5S, 6S, 8R, 10R)-2- bromoethynyl-D3-trishomocubane (27) of C3 symmetry. 1, 3, 5, 7-Tetraethynyladamantane (22), with Td symmetry, was prepared from 1, 3, 5, 7-tetrakis (hydroxymethyl) adamantane (13). Coupling of the C3-component 27 with the Td component 22 was successfully ...