Brasil
| Tesis
Tecnologias em fluxo contínuo de compostos cicloeptânicos derivados da (R)-(–)-carvona e do fragmento C23-C31 usado na síntese total dos policetídeos spirangien A metil éster e spirodienal A
Fecha
2015-05-20Registro en:
Autor
Alves, Leandro de Carvalho
Institución
Resumen
Continuous flow technology of cycloheptanic compounds derived from
(R)-(–)-carvone and the C23-C31 fragment used in the total synthesis of
spirangien A methyl ester and spirodienal A polyketides”
In the first part of this thesis is described the improvement and
development of two synthetic routes to the cycloheptenone 73, in the deca-gram
scale, from the monoterpene (R)-(–)-carvone (58). Were developed reactions in
the continuous flow mode to accelerate and increase the scale production of 73,
and thus avoiding chemical logistics issues.
Sharing the principle of the diversity oriented synthesis and taking
advantage from the cycloheptanic chiron flexibility, were developed α-carbonyl
alkylations followed by catalysis with transition metal, to get, in a fast way,
structurally diverse compounds such as spiro 74, guaiane type 75, xathane 76
and the tris-ketal compound 78.
The second part of this thesis encompasses some results of our
collaboration with Prof. Steven V. Ley CBE FRS and deals with the synthesis
acceleration of the fragment 145 through the usage of continuous flow
processes. The compound 145 is an advanced synthetic intermediate for the
spirangien A (79), spirangien A methyl ester (80) and spirodienal A (81)
syntheses, which are on matter at the Prof. Ley`s group.
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