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Asymmetric bioreduction of a β-tetralone to its corresponding (S)-alcohol by the yeast Trichosporon capitatum MY 1890
The yeast Trichosporon capitatum MY 1890 was identified by microbial screening as a suitable biocatalyst for the asymmetric bioreduction of 6-bromo-β-tetralone to its corresponding (S)-alcoholExpand
Asymmetric Synthesis of MK-0499
Suzuki–Miyaura Cross-Coupling With Quasi-Heterogeneous Palladium
The Suzuki–Miyaura cross-coupling reaction using heterogeneous Pd/C has a homogeneous component. The soluble palladium concentration increases during the reaction reaching a maximum at ca. 90%Expand
Conversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine.
Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions, useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine. Expand
Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration
Mitsunobu reaction of chiral tertiary alcohol (S)-2 with phenol 3 provides the desired ether (R)-1 in moderate yields at elevated temperatures (80–100°C). The SN2 displacement pathway is evident byExpand
Synthesis of a NO-releasing prodrug of rofecoxib.
Two alternate end-game strategies to prepare NO-COXIB 1 from this intermediate were explored and developed: a convergent synthesis where a bromonitrate side chain is introduced in one step and a two-step sequence that first installs the requisite six-carbon ester side chain followed by chemoselective nitration. Expand
Highly Regioselective DABCO‐Catalyzed Nucleophilic Aromatic Substitution (SNAr) Reaction of Methyl 2,6‐Dichloronicotinate with Phenols
Exclusive formation of 6-aryloxy ethers 9 from an S N Ar reaction of methyl 2,6-dichloronicotinate (2) with phenols 7 catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) in the presence ofExpand