Abstract
A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
| Original language | English |
|---|---|
| Pages (from-to) | 8609-8615 |
| Number of pages | 7 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 10 |
| Issue number | 43 |
| DOIs | |
| Publication status | Published - Nov 21 2012 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Biochemistry
Cite this
Stereoconvergent route to chiral cyclohexenone building blocks : Formal synthesis of (-)-dysidiolide. / Moustafa, Gamal A I; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko.
In: Organic and Biomolecular Chemistry, Vol. 10, No. 43, 21.11.2012, p. 8609-8615.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoconvergent route to chiral cyclohexenone building blocks
T2 - Formal synthesis of (-)-dysidiolide
AU - Moustafa, Gamal A I
AU - Kamada, Yasumasa
AU - Tanaka, Tetsuaki
AU - Yoshimitsu, Takehiko
PY - 2012/11/21
Y1 - 2012/11/21
N2 - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
AB - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
UR - http://www.scopus.com/inward/record.url?scp=84867514330&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84867514330&partnerID=8YFLogxK
U2 - 10.1039/c2ob26532j
DO - 10.1039/c2ob26532j
M3 - Article
C2 - 23042006
AN - SCOPUS:84867514330
VL - 10
SP - 8609
EP - 8615
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 43
ER -