Details
| Original language | English |
|---|---|
| Pages (from-to) | 304-319 |
| Number of pages | 16 |
| Journal | Synthesis |
| Issue number | 2 |
| Publication status | Published - 10 Jan 2007 |
Abstract
A practical and stereocontrolled synthetic approach towards the ansa chain of the benzenic ansamycins (mycotrienins) is described, which can be scaled up to multigram quantities. Key features of the synthesis are the formation of the Z-configured tri-substituted double bond by a one-pot esterification of allyl(diisopropoxy)borane and ring-closing metathesis, formation of the β-keto ester via ethyl diazoacetate addition to an aldehyde, and use of the Duthaler-Hafner acetate aldol reaction for the introduction of the stereocenter at C3. The practicality of this synthesis is demonstrated by the preparation of an ansatrienol derivative, representing a formal total synthesis of the ansatrienins.
Keywords
- Aldol reaction, Ansamycin antibiotics, Macrolactamization, Ring-closing metathesis, Total synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis, No. 2, 10.01.2007, p. 304-319.
Research output: Contribution to journal › Review article › Research › peer review
}
TY - JOUR
T1 - A practical synthesis of the ansa chain of benzenic ansamycin antibiotics
T2 - Total synthesis of an ansatrienol derivative
AU - Kashin, Dmitry
AU - Meyer, Axel
AU - Wittenberg, Rüdiger
AU - Schöning, Kai Uwe
AU - Kamlage, Stefan
AU - Kirschning, Andreas
PY - 2007/1/10
Y1 - 2007/1/10
N2 - A practical and stereocontrolled synthetic approach towards the ansa chain of the benzenic ansamycins (mycotrienins) is described, which can be scaled up to multigram quantities. Key features of the synthesis are the formation of the Z-configured tri-substituted double bond by a one-pot esterification of allyl(diisopropoxy)borane and ring-closing metathesis, formation of the β-keto ester via ethyl diazoacetate addition to an aldehyde, and use of the Duthaler-Hafner acetate aldol reaction for the introduction of the stereocenter at C3. The practicality of this synthesis is demonstrated by the preparation of an ansatrienol derivative, representing a formal total synthesis of the ansatrienins.
AB - A practical and stereocontrolled synthetic approach towards the ansa chain of the benzenic ansamycins (mycotrienins) is described, which can be scaled up to multigram quantities. Key features of the synthesis are the formation of the Z-configured tri-substituted double bond by a one-pot esterification of allyl(diisopropoxy)borane and ring-closing metathesis, formation of the β-keto ester via ethyl diazoacetate addition to an aldehyde, and use of the Duthaler-Hafner acetate aldol reaction for the introduction of the stereocenter at C3. The practicality of this synthesis is demonstrated by the preparation of an ansatrienol derivative, representing a formal total synthesis of the ansatrienins.
KW - Aldol reaction
KW - Ansamycin antibiotics
KW - Macrolactamization
KW - Ring-closing metathesis
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=33947536344&partnerID=8YFLogxK
U2 - 10.1055/s-2006-958967
DO - 10.1055/s-2006-958967
M3 - Review article
AN - SCOPUS:33947536344
SP - 304
EP - 319
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 2
ER -