Total synthesis of (+)-γ-lycorane from ethyl lactate using iterative Claisen and Overman rearrangement reactions

Uphade, Manoj B.; Prasad, Kavirayani R.

doi:10.1016/j.tet.2020.131661

Cited by 4 publications

(2 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Prasad et al [184] documented a synthetic method for the synthesis of (+)-γ-lycorane taking advantage of Overman rearrangement. [185,186] Construction of 427 was achieved from phosphonate 426 in eight steps (not shown).…”

Section: Miscellaneousmentioning

confidence: 99%

Synthetic Approaches to α‐, β‐, γ‐, and δ‐Lycoranes

et al. 2023

View full text Add to dashboard Cite

Lycorane is a pentacyclic core presented in alkaloids isolated from the Amaryllidaceae family of herbaceous flowering plants. Members of this class of natural products have shown to display important biological properties including analgesic, antiviral, and antiproliferative activities. This review presents the known synthetic routes toward α‐, β‐, γ‐, and δ‐lycoranes. α‐(19 routes), β‐(10 routes), γ‐(38 routes), and δ‐(6 routes).

show abstract

Section: Miscellaneousmentioning

confidence: 99%

Synthetic Approaches to α‐, β‐, γ‐, and δ‐Lycoranes

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Activities such as AChE inhibitory, anticancer, cytostatic, antivirus, and antifungal activities have been discovered in these natural products. , Among >600 Amaryllidaceae alkaloids, lycorane is a representative of the lycorine class in which three contiguous chiral centers are embedded in a minimally substituted framework . Despite the extensive effort by various research groups to implement an effective total synthesis of lycorane since the first report by Hill and co-workers in 1962, the published synthetic strategies remain mostly racemic, and the asymmetric syntheses, particularly catalytic asymmetric ones, are limited . Furthermore, in known asymmetric methods, a thorny issue, asymmetric total synthesis for all stereoisomers, could not be tackled.…”

mentioning

confidence: 99%