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Synthetic studies on the marine natural product halichondrins
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| Zeitschriftentitel: | Pure and Applied Chemistry |
|---|---|
| Personen und Körperschaften: | , , , , , , , |
| In: | Pure and Applied Chemistry, 75, 2003, 1, S. 1-17 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Walter de Gruyter GmbH
|
| Schlagwörter: |
| author_facet |
Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. |
|---|---|
| author |
Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. |
| spellingShingle |
Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. Pure and Applied Chemistry Synthetic studies on the marine natural product halichondrins General Chemical Engineering General Chemistry |
| author_sort |
choi, hyeong-wook |
| spelling |
Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. 1365-3075 0033-4545 Walter de Gruyter GmbH General Chemical Engineering General Chemistry http://dx.doi.org/10.1351/pac200375010001 <jats:title>Abstract</jats:title> <jats:p>In connection with the de elopment of a practical synthesis of the right half, and its analog E7389, of halichondrin B, an efficient and scalable synthesis of the two major building blocks is reported. In addition, a new synthesis of the C20–C26 segment via a regiospecific and stereoselecti e S<jats:sub>N</jats:sub>2' process is presented. A sulfonamide class of ligands is shown to be effective for asymmetric Ni/Cr-mediated reactions under both stoichiometric and catalytic conditions, and the X-ray structure reveals this class of ligands to be tridentate. On the basis of three X-ray structures, a possible mechanism is suggested for this process. Stable and crystalline Cr(III)/sulfonamide complexes are shown to be effective for catalytic Cr-mediated coupling reactions of allyl, alkenyl, and alkyl halides with aldehydes, and some examples for application of the stoichiometric and catalytic asymmetric processes are presented.</jats:p> Synthetic studies on the marine natural product halichondrins Pure and Applied Chemistry |
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| title |
Synthetic studies on the marine natural product halichondrins |
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Synthetic studies on the marine natural product halichondrins |
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Synthetic studies on the marine natural product halichondrins |
| title_fullStr |
Synthetic studies on the marine natural product halichondrins |
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Synthetic studies on the marine natural product halichondrins |
| title_short |
Synthetic studies on the marine natural product halichondrins |
| title_sort |
synthetic studies on the marine natural product halichondrins |
| topic |
General Chemical Engineering General Chemistry |
| url |
http://dx.doi.org/10.1351/pac200375010001 |
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2003 |
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1-17 |
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<jats:title>Abstract</jats:title>
<jats:p>In connection with the de elopment of a practical synthesis of the right half, and its analog E7389, of halichondrin B, an efficient and scalable synthesis of the two major building blocks is reported. In addition, a new synthesis of the C20–C26 segment via a regiospecific and stereoselecti e S<jats:sub>N</jats:sub>2' process is presented. A sulfonamide class of ligands is shown to be effective for asymmetric Ni/Cr-mediated reactions under both stoichiometric and catalytic conditions, and the X-ray structure reveals this class of ligands to be tridentate. On the basis of three X-ray structures, a possible mechanism is suggested for this process. Stable and crystalline Cr(III)/sulfonamide complexes are shown to be effective for catalytic Cr-mediated coupling reactions of allyl, alkenyl, and alkyl halides with aldehydes, and some examples for application of the stoichiometric and catalytic asymmetric processes are presented.</jats:p> |
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| author | Choi, Hyeong-wook, Demeke, Damtew, Kang, F.-A., Kishi, Y., Nakajima, K., Nowak, P., Wan, Z.-K., Xie, C. |
| author_facet | Choi, Hyeong-wook, Demeke, Damtew, Kang, F.-A., Kishi, Y., Nakajima, K., Nowak, P., Wan, Z.-K., Xie, C., Choi, Hyeong-wook, Demeke, Damtew, Kang, F.-A., Kishi, Y., Nakajima, K., Nowak, P., Wan, Z.-K., Xie, C. |
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| description | <jats:title>Abstract</jats:title> <jats:p>In connection with the de elopment of a practical synthesis of the right half, and its analog E7389, of halichondrin B, an efficient and scalable synthesis of the two major building blocks is reported. In addition, a new synthesis of the C20–C26 segment via a regiospecific and stereoselecti e S<jats:sub>N</jats:sub>2' process is presented. A sulfonamide class of ligands is shown to be effective for asymmetric Ni/Cr-mediated reactions under both stoichiometric and catalytic conditions, and the X-ray structure reveals this class of ligands to be tridentate. On the basis of three X-ray structures, a possible mechanism is suggested for this process. Stable and crystalline Cr(III)/sulfonamide complexes are shown to be effective for catalytic Cr-mediated coupling reactions of allyl, alkenyl, and alkyl halides with aldehydes, and some examples for application of the stoichiometric and catalytic asymmetric processes are presented.</jats:p> |
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| institution | DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1 |
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| physical | 1-17 |
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| spelling | Choi, Hyeong-wook Demeke, Damtew Kang, F.-A. Kishi, Y. Nakajima, K. Nowak, P. Wan, Z.-K. Xie, C. 1365-3075 0033-4545 Walter de Gruyter GmbH General Chemical Engineering General Chemistry http://dx.doi.org/10.1351/pac200375010001 <jats:title>Abstract</jats:title> <jats:p>In connection with the de elopment of a practical synthesis of the right half, and its analog E7389, of halichondrin B, an efficient and scalable synthesis of the two major building blocks is reported. In addition, a new synthesis of the C20–C26 segment via a regiospecific and stereoselecti e S<jats:sub>N</jats:sub>2' process is presented. A sulfonamide class of ligands is shown to be effective for asymmetric Ni/Cr-mediated reactions under both stoichiometric and catalytic conditions, and the X-ray structure reveals this class of ligands to be tridentate. On the basis of three X-ray structures, a possible mechanism is suggested for this process. Stable and crystalline Cr(III)/sulfonamide complexes are shown to be effective for catalytic Cr-mediated coupling reactions of allyl, alkenyl, and alkyl halides with aldehydes, and some examples for application of the stoichiometric and catalytic asymmetric processes are presented.</jats:p> Synthetic studies on the marine natural product halichondrins Pure and Applied Chemistry |
| spellingShingle | Choi, Hyeong-wook, Demeke, Damtew, Kang, F.-A., Kishi, Y., Nakajima, K., Nowak, P., Wan, Z.-K., Xie, C., Pure and Applied Chemistry, Synthetic studies on the marine natural product halichondrins, General Chemical Engineering, General Chemistry |
| title | Synthetic studies on the marine natural product halichondrins |
| title_full | Synthetic studies on the marine natural product halichondrins |
| title_fullStr | Synthetic studies on the marine natural product halichondrins |
| title_full_unstemmed | Synthetic studies on the marine natural product halichondrins |
| title_short | Synthetic studies on the marine natural product halichondrins |
| title_sort | synthetic studies on the marine natural product halichondrins |
| title_unstemmed | Synthetic studies on the marine natural product halichondrins |
| topic | General Chemical Engineering, General Chemistry |
| url | http://dx.doi.org/10.1351/pac200375010001 |