91366-13-1Relevant articles and documents
Stereochemical studies on the reactions catalyzed by the PLP-dependent enzyme 1-aminocyclopropane-1-carboxylate deaminase
Liu,Auchus,Walsh
, p. 5335 - 5348 (1984)
The stereochemical course of 1-aminocyclopropane-1-carboxylate deaminase which catalyzes the fragmentation of the cyclopropane substrate to alpha -ketobutyrate and ammonia has been unraveled with the help of substrates stereospecifically labeled with deuterium and/or tritium, and this has afforded important information about the process occurring at the active site during enzymatic conversion.
Methods for preparing antiviral calanolide compounds
-
Example 23, (2008/06/13)
The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.
