A Most Recent Approach for the Stereoselective Synthesis of (+)­epi­Cytoxazone

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A Most Recent Approach for the Stereoselective Synthesis of (+)­epi­Cytoxazone

September 17, 2020 Chemical Science 0

Discovery of the biological potentialities of cytoxazone by Kakeya’s research group has leveraged the
development of studies aimed at the synthesis of this compound. The stereoselective total synthesis
of (+)-
epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route
from 2,3-
O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular
control of the target molecule’s asymmetric centers in the dihydroxylation step by promoting the
approach of OsO
4 to the face opposite to that of the ketal group. In this study, the authors proposed
that 5-
epi-cytoxazone (1) may be prepared by an N,O-heterocyclization reaction of the corresponding
amino alcohol (
8) in the last step of the synthesis.

Author (s) Details

Izabel L. Miranda
Departamento de Química, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil.

Suélen K. Sartori
Departamento de Química, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil.

Marisa A. N. Diaz
Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Viçosa, 36570-900 Viçosa-MG, Brazil.

Gaspar Diaz­Muñoz
Departamento de Química, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil.

View Book :- https://bp.bookpi.org/index.php/bpi/catalog/book/253

 

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