Details
| Original language | English |
|---|---|
| Pages (from-to) | 1624-1626 |
| Number of pages | 3 |
| Journal | Synlett |
| Issue number | 10 |
| Publication status | Published - 31 Dec 1999 |
| Externally published | Yes |
Abstract
A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien l), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.
Keywords
- Evans-aldolation, Homer-Emmons olefination, Macrolactam antibiotic
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Synlett, No. 10, 31.12.1999, p. 1624-1626.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Stereocontrolled preparation of the C1-C14 polyene fragment of benzenic ansamycin antibiotics ansatrienin A and B
AU - Schöning, Kai Uwe
AU - Wittenberg, Rüdiger
AU - Kirschning, Andreas
PY - 1999/12/31
Y1 - 1999/12/31
N2 - A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien l), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.
AB - A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien l), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.
KW - Evans-aldolation
KW - Homer-Emmons olefination
KW - Macrolactam antibiotic
UR - http://www.scopus.com/inward/record.url?scp=0344563618&partnerID=8YFLogxK
U2 - 10.1055/s-1999-2888
DO - 10.1055/s-1999-2888
M3 - Article
AN - SCOPUS:0344563618
SP - 1624
EP - 1626
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 10
ER -