1259290-59-9Relevant academic research and scientific papers
Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis
Barthel, André,Kaden, Felix,J?ger, Anne,Metz, Peter
, p. 3298 - 3301 (2016)
Relay metathesis enabled an improved access from (S)-citronellal to the marine trisnorguaiane (-)-clavukerin A. This hydroazulene was applied as an advantageously functionalized building block for the asymmetric synthesis of the sesquiterpene lactone osmitopsin and the proposed structure of 4,5-epoxyosmitopsin using a chemo-, regio-, and diastereoselective diepoxide opening as the key step.
A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A
Knueppel, Stephan,Rogachev, Victor O.,Metz, Peter
, p. 6145 - 6148 (2010)
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.
