Details
| Original language | English |
|---|---|
| Title of host publication | Natural Product Synthesis II |
| Subtitle of host publication | Targets, Methods, Concepts |
| Editors | Johann Mulzer |
| Pages | 43-76 |
| Number of pages | 34 |
| Publication status | Published - 26 Jan 2005 |
Publication series
| Name | Topics in Current Chemistry |
|---|---|
| Volume | 244 |
| ISSN (Print) | 0340-1022 |
Abstract
The synthesis of complex natural products still remains as the bottleneck for the biological evaluation of such compounds. In contrast to the biosyntheses, vinylogous aldol reactions can incorporate more than one acetate or propionate building block into the growing polyketide chain. To facilitate such reactions either enolate activation or aldehyde activation is required. For both variations, selective protocols have been put forward and were shown to be efficient substitutes compared to standard aldol reactions. As can be seen in the total syntheses of natural products such as callipeltoside, their use shortens the synthetic route significantly. One of the most challenging transformations in this context is the use of γ-substituted ketene acetals in both aldehyde and enolate activation. In particular, aliphatic aldehydes give poor yields and selectivities. Protocols for the enantioselective variation are given using either the Tol-BINAP system or C2-symmetrical copper(II) complexes.
Keywords
- Aldol reaction, Callipeltoside, Lewis acid, Vinylogous
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
Cite this
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Natural Product Synthesis II: Targets, Methods, Concepts. ed. / Johann Mulzer. 2005. p. 43-76 (Topics in Current Chemistry; Vol. 244).
Research output: Chapter in book/report/conference proceeding › Contribution to book/anthology › Research › peer review
}
TY - CHAP
T1 - Recent advances in vinylogous aldol reactions and their applications in the syntheses of natural products
AU - Kalesse, Markus
PY - 2005/1/26
Y1 - 2005/1/26
N2 - The synthesis of complex natural products still remains as the bottleneck for the biological evaluation of such compounds. In contrast to the biosyntheses, vinylogous aldol reactions can incorporate more than one acetate or propionate building block into the growing polyketide chain. To facilitate such reactions either enolate activation or aldehyde activation is required. For both variations, selective protocols have been put forward and were shown to be efficient substitutes compared to standard aldol reactions. As can be seen in the total syntheses of natural products such as callipeltoside, their use shortens the synthetic route significantly. One of the most challenging transformations in this context is the use of γ-substituted ketene acetals in both aldehyde and enolate activation. In particular, aliphatic aldehydes give poor yields and selectivities. Protocols for the enantioselective variation are given using either the Tol-BINAP system or C2-symmetrical copper(II) complexes.
AB - The synthesis of complex natural products still remains as the bottleneck for the biological evaluation of such compounds. In contrast to the biosyntheses, vinylogous aldol reactions can incorporate more than one acetate or propionate building block into the growing polyketide chain. To facilitate such reactions either enolate activation or aldehyde activation is required. For both variations, selective protocols have been put forward and were shown to be efficient substitutes compared to standard aldol reactions. As can be seen in the total syntheses of natural products such as callipeltoside, their use shortens the synthetic route significantly. One of the most challenging transformations in this context is the use of γ-substituted ketene acetals in both aldehyde and enolate activation. In particular, aliphatic aldehydes give poor yields and selectivities. Protocols for the enantioselective variation are given using either the Tol-BINAP system or C2-symmetrical copper(II) complexes.
KW - Aldol reaction
KW - Callipeltoside
KW - Lewis acid
KW - Vinylogous
UR - http://www.scopus.com/inward/record.url?scp=30744451484&partnerID=8YFLogxK
U2 - 10.1007/b96887
DO - 10.1007/b96887
M3 - Contribution to book/anthology
AN - SCOPUS:30744451484
SN - 3540211241
SN - 9783540211242
T3 - Topics in Current Chemistry
SP - 43
EP - 76
BT - Natural Product Synthesis II
A2 - Mulzer, Johann
ER -