Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway.

Autor: Tao J; Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, USA., Hu S, Pacholec M, Walsh CT
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2003 Sep 04; Vol. 5 (18), pp. 3233-6.
DOI: 10.1021/ol035101r
Abstrakt: [structure: see text] A chemoenzymatic synthesis was described to prepare proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway. The successful synthesis of these fragile molecules relies heavily on mild enzymatic deprotection and efficient enzymatic kinetic resolution to minimize epimerization, decomposition, multiple orthogonal protections, and retro aldol reactions often encountered in their chemical synthesis.
Databáze: MEDLINE