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Synlett 1991; 1991(9): 614-617
DOI: 10.1055/s-1991-20815
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Total Synthesis of 22,23-Dihydroavermectin B1b Aglycone

Jean Pierre Férézou* , Marc Julia, Lu Wei Liu, Ange Pancrazi
  • *Laboratoire de Chime, École Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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07. März 2002 (online)

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The total synthesis of the aglycone of 22,23-dihydroavermectin B1b involves a palladium(0) catalysed cross-coupling reaction between a C10-C25 northern E-vinylstannane and a C1-C9 vinyl iodide where the Δ3 double bond as well as the correct stereochemistry at C - 2 are already present. The final steps include successive deprotection of the carboxyl β-(trimethylsilyl)ethyl protecting group of the intermediate secoester, macrolactonisation and acidic hydrolysis of 5-O-tert-butyldimethylsilyl residue to give the title aglycone.