Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2483-2491 |
| Seitenumfang | 9 |
| Fachzeitschrift | Chemistry - a European journal |
| Jahrgang | 5 |
| Ausgabenummer | 9 |
| Frühes Online-Datum | 30 Aug. 1999 |
| Publikationsstatus | Veröffentlicht - 3 Sept. 1999 |
| Extern publiziert | Ja |
Abstract
The total synthesis of (-)-epothilone A by a convergent route is reported. The synthesis of the required key intermediates has been improved with respect to stereoselectivity and availability. The access to ethyl ketone 2 has been significantly improved by employment of chiral acetate equivalents, which provided higher optical and chemical yields. Key intermediate 3 was obtained by oxazolidinone auxiliary techniques and stereoselectively coupled with 2 by an aldol reaction. After esterification with thiazole fragment 4, (-)-epothilone A was finally constructed by using ring-closing metathesis.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Organische Chemie
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in: Chemistry - a European journal, Jahrgang 5, Nr. 9, 03.09.1999, S. 2483-2491.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Total synthesis of (-)-epothilone A
AU - Schinzer, Dieter
AU - Bauer, Armin
AU - Böhm, Oliver M.
AU - Limberg, Anja
AU - Cordes, Martin
PY - 1999/9/3
Y1 - 1999/9/3
N2 - The total synthesis of (-)-epothilone A by a convergent route is reported. The synthesis of the required key intermediates has been improved with respect to stereoselectivity and availability. The access to ethyl ketone 2 has been significantly improved by employment of chiral acetate equivalents, which provided higher optical and chemical yields. Key intermediate 3 was obtained by oxazolidinone auxiliary techniques and stereoselectively coupled with 2 by an aldol reaction. After esterification with thiazole fragment 4, (-)-epothilone A was finally constructed by using ring-closing metathesis.
AB - The total synthesis of (-)-epothilone A by a convergent route is reported. The synthesis of the required key intermediates has been improved with respect to stereoselectivity and availability. The access to ethyl ketone 2 has been significantly improved by employment of chiral acetate equivalents, which provided higher optical and chemical yields. Key intermediate 3 was obtained by oxazolidinone auxiliary techniques and stereoselectively coupled with 2 by an aldol reaction. After esterification with thiazole fragment 4, (-)-epothilone A was finally constructed by using ring-closing metathesis.
KW - Cytotoxic agents
KW - Epothilones
KW - Macrolides
KW - Natural products
UR - http://www.scopus.com/inward/record.url?scp=0032869834&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N
DO - 10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N
M3 - Article
AN - SCOPUS:0032869834
VL - 5
SP - 2483
EP - 2491
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 9
ER -