Details
| Original language | English |
|---|---|
| Pages (from-to) | 2483-2491 |
| Number of pages | 9 |
| Journal | Chemistry - a European journal |
| Volume | 5 |
| Issue number | 9 |
| Early online date | 30 Aug 1999 |
| Publication status | Published - 3 Sept 1999 |
| Externally published | Yes |
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.
Keywords
- Cytotoxic agents, Epothilones, Macrolides, Natural products
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 5, No. 9, 03.09.1999, p. 2483-2491.
Research output: Contribution to journal › Article › Research › 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 -