A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A

Stephan Knüppel, Victor O. Rogachev, Peter Metz

Результат исследований: Материалы для журналаСтатьярецензирование

22 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаАнглийский
Страницы (с-по)6145-6148
Число страниц4
ЖурналEuropean Journal of Organic Chemistry
Номер выпуска32
DOI
СостояниеОпубликовано - 1 ноя 2010
Опубликовано для внешнего пользованияДа

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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