Premium
Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J
Author(s) -
Trentadue Kathryn,
Chang ChiaFu,
Nalin Ansel,
Taylor Richard E.
Publication year - 2021
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.202100975
Subject(s) - enantioselective synthesis , polyketide , biosynthesis , stereochemistry , pyran , polyketide synthase , total synthesis , stereoselectivity , chemistry , natural product , diol , convergent synthesis , biochemistry , biology , combinatorial chemistry , enzyme , organic chemistry , catalysis
Abstract The family of anti‐fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki‐Miyaura cross‐coupling and a Julia‐Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.