Ring expansions of (R)-(–)-carvone to cycloheptenoid chirons

Ring expansions of (R)-(–)-carvone to cycloheptenoid chirons

Alves, Leandro de C.; Desiderá, André L.; Oliveira, Kleber T. de; Brocksom, Timothy J.

Abstract:

In the course of our studies on the synthesis of perhydroazulene terpenes, we have developed a synthetic route (Scheme 1, Route A) to the cycloheptenone chiron 6 from (R)-(–)-carvone (1). Herein we present our corrected structural assignment of 4a, as confirmed by X-ray analysis, and describe an attractive alternative route towards 6 (Scheme 1, Route B).

In the course of our studies on the synthesis of perhydroazulene terpenes, we have developed a synthetic route (Scheme 1, Route A) to the cycloheptenone chiron 6 from (R)-(–)-carvone (1). Herein we present our corrected structural assignment of 4a, as confirmed by X-ray analysis, and describe an attractive alternative route towards 6 (Scheme 1, Route B).

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201396163412

Referências bibliográficas

• [1] 1 Brocksom, T. J., Brocksom, U., Sousa, D. P, Frederico, D. Tetrahedron Asym., 2005, 16, 362. Faria, M. L; Magalhães, R. A.; Silva, F. C.; Matias, L. G. O.; Ceschi, M. A.; Brocksom, U; Brocksom, T. J. Tetrahedron Asym., 2000,11, 4093
• [2] 2. Alves, L de C.; et al. 14th BMOS, 2011.

Como citar:

Alves, Leandro de C.; Desiderá, André L.; Oliveira, Kleber T. de; Brocksom, Timothy J.; "Ring expansions of (R)-(–)-carvone to cycloheptenoid chirons", p-117-117. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201396163412