Abstract
Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.
| Original language | English |
|---|---|
| Pages (from-to) | 3175-3177 |
| Number of pages | 3 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 43 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2004 Jun 14 |
| Externally published | Yes |
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Keywords
- Alcohols
- Aldol reaction
- Lactones
- Natural products
- Total synthesis
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Highly efficient total synthesis of (+)-citreoviral. / Murata, Yoshihisa; Kamino, Tomoyuki; Aoki, Toshiaki; Hosokawa, Seijiro; Kobayashi, Susumu.
In: Angewandte Chemie - International Edition, Vol. 43, No. 24, 14.06.2004, p. 3175-3177.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly efficient total synthesis of (+)-citreoviral
AU - Murata, Yoshihisa
AU - Kamino, Tomoyuki
AU - Aoki, Toshiaki
AU - Hosokawa, Seijiro
AU - Kobayashi, Susumu
PY - 2004/6/14
Y1 - 2004/6/14
N2 - Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.
AB - Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.
KW - Alcohols
KW - Aldol reaction
KW - Lactones
KW - Natural products
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=4544311529&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4544311529&partnerID=8YFLogxK
U2 - 10.1002/anie.200454212
DO - 10.1002/anie.200454212
M3 - Article
VL - 43
SP - 3175
EP - 3177
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 24
ER -