Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)–C(15) Segment | Zendy

Sheila Namirembe | Zendy; Yan Lü | Zendy; James P. Morken | Zendy

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Studies 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.

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