The analysis of two distinct strategies toward the enantioselective formal total synthesis of (+)-Gelsenicine

A 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 Gelse-mium alkaloid syntheses.(c) 2023 Elsevier Ltd. All rights reserved.

Automated summary

This article describes a comprehensive and enantioselective total synthesis of (+)-gelsenicine. Two different strategies based on catalytic cycloisomerization as the central step are proposed. One strategy involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, whereas the latter strategy utilizes phosphoramidite- and bisphosphine-gold complexes to provide a high enantiopurity key intermediate in the Gelsemium alkaloid syntheses. (c) 2023 Elsevier Ltd. All rights reserved.