Abstract
(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.
| Original language | English |
|---|---|
| Pages (from-to) | 4843-4848 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 45 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - 2006 Jul 17 |
| Externally published | Yes |
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Keywords
- Aldol reaction
- Asymmetric synthesis
- Medium-ring compounds
- Protecting groups
- Terpenoids
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Asymmetric total synthesis of (-)-merrilactone A : Use of a bulky protecting group as long-range stereocontrolling element. / Inoue, Masayuki; Satou, Takaaki; Hirama, Masahiro.
In: Angewandte Chemie - International Edition, Vol. 45, No. 29, 17.07.2006, p. 4843-4848.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Asymmetric total synthesis of (-)-merrilactone A
T2 - Use of a bulky protecting group as long-range stereocontrolling element
AU - Inoue, Masayuki
AU - Satou, Takaaki
AU - Hirama, Masahiro
PY - 2006/7/17
Y1 - 2006/7/17
N2 - (Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.
AB - (Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.
KW - Aldol reaction
KW - Asymmetric synthesis
KW - Medium-ring compounds
KW - Protecting groups
KW - Terpenoids
UR - http://www.scopus.com/inward/record.url?scp=33746787198&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33746787198&partnerID=8YFLogxK
U2 - 10.1002/anie.200601358
DO - 10.1002/anie.200601358
M3 - Article
C2 - 16795104
AN - SCOPUS:33746787198
VL - 45
SP - 4843
EP - 4848
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 29
ER -