Abstract
Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products. A combination of an organocatalytic Michael addition and a ruthenium-catalyzed dienyne metathesis allowed efficient access to the enantiopure title hydroazulenes from (S)- and (R)-citronellal, respectively, in only four steps.
| Original language | English |
|---|---|
| Pages (from-to) | 6145-6148 |
| Number of pages | 4 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 32 |
| DOIs | |
| Publication status | Published - 1 Nov 2010 |
| Externally published | Yes |
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Keywords
- Domino reactions
- Metathesis
- Michael addition
- Organocatalysis
- Ruthenium
- Terpenoids
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A. / Knüppel, Stephan; Rogachev, Victor O.; Metz, Peter.
In: European Journal of Organic Chemistry, No. 32, 01.11.2010, p. 6145-6148.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A
AU - Knüppel, Stephan
AU - Rogachev, Victor O.
AU - Metz, Peter
PY - 2010/11/1
Y1 - 2010/11/1
N2 - Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products. A combination of an organocatalytic Michael addition and a ruthenium-catalyzed dienyne metathesis allowed efficient access to the enantiopure title hydroazulenes from (S)- and (R)-citronellal, respectively, in only four steps.
AB - Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products. A combination of an organocatalytic Michael addition and a ruthenium-catalyzed dienyne metathesis allowed efficient access to the enantiopure title hydroazulenes from (S)- and (R)-citronellal, respectively, in only four steps.
KW - Domino reactions
KW - Metathesis
KW - Michael addition
KW - Organocatalysis
KW - Ruthenium
KW - Terpenoids
UR - http://www.scopus.com/inward/record.url?scp=78249268215&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78249268215&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201001087
DO - 10.1002/ejoc.201001087
M3 - Article
AN - SCOPUS:78249268215
SP - 6145
EP - 6148
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 32
ER -