Details
| Original language | English |
|---|---|
| Pages (from-to) | 14038-14039 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 128 |
| Issue number | 43 |
| Publication status | Published - 1 Nov 2006 |
Abstract
The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemical Engineering(all)
- Colloid and Surface Chemistry
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In: Journal of the American Chemical Society, Vol. 128, No. 43, 01.11.2006, p. 14038-14039.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The total synthesis of (+)-tedanolide
AU - Ehrlich, Gunnar
AU - Hassfeld, Jorma
AU - Eggert, Ulrike
AU - Kalesse, Markus
PY - 2006/11/1
Y1 - 2006/11/1
N2 - The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.
AB - The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.
UR - http://www.scopus.com/inward/record.url?scp=33750434287&partnerID=8YFLogxK
U2 - 10.1021/ja0659572
DO - 10.1021/ja0659572
M3 - Article
C2 - 17061881
AN - SCOPUS:33750434287
VL - 128
SP - 14038
EP - 14039
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 43
ER -