Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

Cytoxazone, originally isolated from cultures of a Streptomyces species has an oxazolidin-2-one 4,5-disubstituted ring. It is known that this natural product presents a cytokine modulator effect through the signaling pathway of Th2 cells (type 2 cytokines), which are involved in the process of growth and differentiation of cells. From this, the interest in the development of research aimed at the total synthesis of this molecule and its analogs has remained high, which can be confirmed by the large number of publications on the topic, more than 30 to date. This review focuses on the various creative methods for the synthesis of (−)-cytoxazone and its congeners. The assessment of the preparation of this oxazolidinone and related structures serves as a treatise on the efforts made in the synthesis of this important class of compound from its first total synthesis in 1999.

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“…Oxazolidin-2-one rings 51 and 52 were formed Scheme 6. Synthesis of (−)-cytoxazone via stereoselective Grignard addition [18].…”

Section: Short Synthesis Of Both Enantiomers Of Cytoxazone Using the Petasis Reactionmentioning

confidence: 99%

Synthesis Approaches to (−)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures

Miranda¹,

Lopes²,

Diaz³

et al. 2019

Top 5 Contributions in Molecular Sciences

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“…In another contribution to the preparation of (−)-cytoxazone, Rao and co-workers [18] proposed a stereoselective addition reaction of a vinyl Grignard at the N -Boc-aldehyde 34a , obtained from p -hydroxy-D-phenylglycine ( 31 , Scheme 6). Starting from 31 , the sequence of esterification, N -Boc-protection, phenol methylation, and the reduction of the ester function generated alcohol 34 in 81.6% yield (four steps).…”

Section: Total Synthesis Strategies Of (−)-Cytoxazone and Congenersmentioning

confidence: 99%

Synthesis Approaches to (−)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures

et al. 2016

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(−)-Cytoxazone, originally isolated from cultures of a Streptomyces species has an oxazolidin-2-one 4,5-disubstituted ring. It is known that this natural product presents a cytokine modulator effect through the signaling pathway of Th2 cells (type 2 cytokines), which are involved in the process of growth and differentiation of cells. From this, the interest in the development of research aimed at the total synthesis of this molecule and its analogs has remained high, which can be confirmed by the large number of publications on the topic, more than 30 to date. This review focuses on the various creative methods for the synthesis of (−)-cytoxazone and its congeners. The assessment of the preparation of this oxazolidinone and related structures serves as a treatise on the efforts made in the synthesis of this important class of compound from its first total synthesis in 1999.

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