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Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.

ABSTRACT: 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 ?-hydroxy allylic alcohols was explored to stereoselectively construct ?,?'-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.

SUBMITTER: Lanier ML 

PROVIDER: S-EPMC5653968 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.

Lanier Megan L ML   Park Hyeri H   Mukherjee Paramita P   Timmerman Jacob C JC   Ribeiro Anthony A AA   Widenhoefer Ross A RA   Hong Jiyong J  

Chemistry (Weinheim an der Bergstrasse, Germany) 20170503 30

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 molecu  ...[more]

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