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Formal Synthesis of (+)‐Laurencin by Gold(I)‐Catalyzed Intramolecular Dehydrative Alkoxylation
Author(s) -
Lanier Megan L.,
Park Hyeri,
Mukherjee Paramita,
Timmerman Jacob C.,
Ribeiro Anthony A.,
Widenhoefer Ross A.,
Hong Jiyong
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700499
Subject(s) - intramolecular force , catalysis , chemistry , formal synthesis , medicinal chemistry , organic chemistry
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.