1190754-14-3Relevant academic research and scientific papers
Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library
Welford, Amanda J,Caldwell, John J.,Liu, Manjuan,Richards, Meirion,Brown, Nathan,Lomas, Cara,Tizzard, Graham J.,Pitak, Mateusz B.,Coles, Simon J.,Eccles, Suzanne A.,Raynaud, Florence I.,Collins, Ian
, p. 5657 - 5664 (2016)
The 2,11-cembranoid family of natural products has been used as inspiration for the synthesis of a structurally simplified, functionally diverse library of octahydroisobenzofuran-based compounds designed to augment a typical medicinal chemistry library screen. Ring-closing metathesis, lactonisation and SmI2-mediated methods were exemplified and applied to the installation of a third ring to mimic the nine-membered ring of the 2,11-cembranoids. The library was assessed for aqueous solubility and permeability, with a chemical-space analysis performed for comparison to the family of cembranoid natural products and a sample set of a screening library. Preliminary investigations in cancer cells showed that the simpler scaffolds could recapitulate the reported anti-migratory activity of the natural products. Building a bridge: A library of compounds based on the naturally occurring 2,11-cembranoid family has been synthesised by using different synthetic strategies. The library was found to cover the space between the natural products and a screening library sample set (see figure). The new compounds were shown to recapitulate reported activities of the natural products.
Cycloaddition and one-carbon homologation studies in the synthesis of advanced iridoid precursors
Stevens, Anne T.,Caira, Mino R.,Bull, James R.,Chibale, Kelly
supporting information; experimental part, p. 3527 - 3536 (2010/01/06)
A Diels-Alder cycloaddition approach to the sweroside aglycone intermediate of iridoids was explored using silylated butenolides and levoglucosenone as dienophiles under both Lewis acid and thermal conditions. Results of this study reveal no evidence that
