Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation
8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α′-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.
Lanier, Megan L.,Park, Hyeri,Mukherjee, Paramita,Timmerman, Jacob C.,Ribeiro, Anthony A.,Widenhoefer, Ross A.,Hong, Jiyong
supporting information
p. 7180 - 7184
(2017/05/31)
First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid
The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd0/Cu I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.
Rodríguez, Ana R.,Spur, Bernd W.
p. 3623 - 3627
(2007/10/03)
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