New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone
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 th...
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| Published in | Journal of the Brazilian Chemical Society Vol. 30; no. 3; pp. 585 - 591 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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SAO PAULO
Soc Brasileira Quimica
01.03.2019
Sociedade Brasileira de Química |
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| Abstract | 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 OsO4 to the face opposite to that of the ketal group. |
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| AbstractList | 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 OsO4 to the face opposite to that of the ketal group. |
| Author | Diaz, Marisa A. N. Sartori, Suelen K. Miranda, Izabel L. Diaz-Munoz, Gaspar |
| AuthorAffiliation | Universidade Federal de Viçosa Universidade Federal de Minas Gerais |
| AuthorAffiliation_xml | – sequence: 0 name: Universidade Federal de Viçosa – sequence: 0 name: Universidade Federal de Minas Gerais |
| Author_xml | – sequence: 1 givenname: Izabel L. surname: Miranda fullname: Miranda, Izabel L. organization: Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil – sequence: 2 givenname: Suelen K. surname: Sartori fullname: Sartori, Suelen K. organization: Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil – sequence: 3 givenname: Marisa A. N. orcidid: 0000-0002-3370-4149 surname: Diaz fullname: Diaz, Marisa A. N. organization: Univ Fed Vicosa, Dept Bioquim & Biol Mol, BR-36570900 Vicosa, MG, Brazil – sequence: 4 givenname: Gaspar surname: Diaz-Munoz fullname: Diaz-Munoz, Gaspar email: gaspardm@qui.ufmg.br organization: Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil |
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| Cites_doi | 10.1016/j.tet.2006.03.079 10.1021/ja500374p 10.1016/j.tetlet.2017.11.057 10.1021/jo101559p 10.1039/c4cc06395c 10.1021/jo010270f 10.1081/SCC-200048953 10.1016/j.tetlet.2017.07.044 10.3390/molecules19067429 10.1080/00397910600619499 10.1081/SCC-120022181 10.1021/ja044461m 10.1021/jo026832s 10.3390/molecules21091176 10.1016/j.ijantimicag.2003.11.003 10.1021/ja800746q |
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| Keywords | stereoselective dihydroxylation epi-cytoxazone Wittig olefination cytoxazone RING 2,3-O-(3-pentylidene)-(R)-glyceraldehyde CYTOKINE MODULATOR VERSATILE SYNTHESIS OXAZOLIDINONES (-)-CYTOXAZONE |
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| Snippet | The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from... |
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| Title | New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone |
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