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 |
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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 |
Keywords
- Domino reactions
- Metathesis
- Michael addition
- Organocatalysis
- Ruthenium
- Terpenoids
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry