The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine

Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.PMID:37034426 | PMC:PMC10077972 | DOI:10.1016/j.tet.2023.133278

Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research