106622-88-2Relevant articles and documents
Synthesis of pluraflavin A "aglycone"
Wright, Benjamin J. D.,Hartung, John,Peng, Feng,Van De Water, Ryan,Liu, Haibo,Tan, Quen-Hui,Chou, Ting-Chao,Danishefsky, Samuel J.
supporting information; experimental part, p. 16786 - 16790 (2009/04/14)
The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the γ-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.
SUBSTRATE SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Lazzarini, Ameriga,Casati, Paolo
, p. 2575 - 2582 (2007/10/02)
Penicillinacylase from E. coli, immobilized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23 deg C, of a set of O-phenylacetate esters of primary carbinols.The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework.Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and Sepharose-bound enzyme.
Natural polyene α-pyrones. Synthesis of (+)-citreoviral
Bowden,Patel,Pattenden
, p. 4793 - 4796 (2007/10/02)
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