Details
| Original language | English |
|---|---|
| Pages (from-to) | 11210-11212 |
| Number of pages | 3 |
| Journal | Chemistry - a European journal |
| Volume | 22 |
| Issue number | 32 |
| Early online date | 15 Jun 2016 |
| Publication status | Published - 27 Jul 2016 |
Abstract
The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.
Keywords
- aetheramide, anti-HIV, macrocyclization, structure elucidation, vinylogous Mukaiyama aldol reaction
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Chemistry - a European journal, Vol. 22, No. 32, 27.07.2016, p. 11210-11212.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total Synthesis of Aetheramide A
AU - Gerstmann, Lisa
AU - Kalesse, Markus
PY - 2016/7/27
Y1 - 2016/7/27
N2 - The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.
AB - The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.
KW - aetheramide
KW - anti-HIV
KW - macrocyclization
KW - structure elucidation
KW - vinylogous Mukaiyama aldol reaction
UR - http://www.scopus.com/inward/record.url?scp=84979660338&partnerID=8YFLogxK
U2 - 10.1002/chem.201602682
DO - 10.1002/chem.201602682
M3 - Article
C2 - 27303862
AN - SCOPUS:84979660338
VL - 22
SP - 11210
EP - 11212
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 32
ER -