Details
| Original language | English |
|---|---|
| Pages (from-to) | 2817-2823 |
| Number of pages | 7 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 11 |
| Publication status | Published - Nov 1999 |
Abstract
The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.
Keywords
- Aldol reactions, Diastereoselective alkylation, Epothilone A, Lactones, Ring-closing metathesis
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 11, 11.1999, p. 2817-2823.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The formal total synthesis of epothilone A
AU - Kalesse, Markus
AU - Quitschalle, Monika
AU - Claus, Eckhard
AU - Gerlach, Kai
AU - Pahl, Axel
AU - Meyer, Hartmut H.
PY - 1999/11
Y1 - 1999/11
N2 - The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.
AB - The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.
KW - Aldol reactions
KW - Diastereoselective alkylation
KW - Epothilone A
KW - Lactones
KW - Ring-closing metathesis
UR - http://www.scopus.com/inward/record.url?scp=0032698282&partnerID=8YFLogxK
U2 - 10.1002/(sici)1099-0690(199911)1999:11<2817::aid-ejoc2817>3.0.co;2-l
DO - 10.1002/(sici)1099-0690(199911)1999:11<2817::aid-ejoc2817>3.0.co;2-l
M3 - Article
AN - SCOPUS:0032698282
SP - 2817
EP - 2823
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 11
ER -