872831-34-0Relevant academic research and scientific papers
An intramolecular Diels-Alder strategy for the asbestinins: Enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12
Crimmins, Michael T.,Ellis, J. Michael
, p. 1649 - 1660 (2008/09/18)
(Chemical Equation Presented) The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.
Establishing the absolute configuration of the asbestinins: Enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D
Crimmins, Michael T.,Ellis, J. Michael
, p. 17200 - 17201 (2007/10/03)
A highly stereoselective synthesis of 11-acetoxy-4-deoxyasbestinin D (1) has been completed in 26 linear steps. The synthesis hinges on a selective glycolate aldol addition to establish the C-2 stereocenter, a ring-closing metathesis reaction to complete the oxonene, and an intramolecular Diels-Alder cycloaddition to establish the relative configuration at C-1, C-10, and C-14. This initial total synthesis of an asbestinin also serves to confirm the absolute configuration of this subclass of the C-2-C-11-cyclized cembranoid natural products. Copyright
