Open AccessStudies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)–C(15) Segment
Author(s) -
Sheila Namirembe,
Yan Lü,
James P. Morken
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03134
Subject(s) - chemistry , enantioselective synthesis , intramolecular force , stereoselectivity , alkene , stereochemistry , tetrahydrofuran , wittig reaction , total synthesis , catalysis , natural product , conjugate , medicinal chemistry , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics , solvent
An enantioselective synthesis of the C(1)-C(15) segment of the marine natural product amphidinolide C has been accomplished by a route that includes a stereoselective boron-Wittig reaction to furnish a trisubstituted alkenylboronate. In addition, the route employs enantioselective alkene diboration to install the C(6) hydroxyl group which undergoes intramolecular conjugate addition to establish a tetrahydrofuran ring. Lastly, a catalytic Suzuki-Miyaura cross-coupling is accomplished to construct the C(9)-C(10) bond.