Benkhoff, Johannes; Boese, Roland; Klaemer, Frank Gerrit; Wigger, Arne E.:

Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive Diels-Alder reactions.

In: Tetrahedron letters (Tetrahedron Lett.), Jg. 35 (1994) ; Nr. 1, S. 73-76
ISSN: 0040-4039
Zeitschriftenaufsatz / Fach: Chemie
Synthesis of the syn-dimethanotetrahydroanthracene and -tetracene derivs. I (R1 = R2 = OMe, OH, OAc; R1 = Me, R2 = OH 2a-d) and II (R3 = OMe, OH 6a, b) are described. Highly stereoselective, pressure-induced repetitive Diels-Alder reactions of these bis-dienophiles with bis-diene III (7) lead to sterically rigid macrocycles having well defined cavities of different size.