Total Synthesis of Racemic (±)-Parvistemonine A

Abstract

Parvistemonine A was isolated from Stemona parviflora. The total synthesis of racemic parvistemonine A was completed in 6 steps for the first time, employing compound 7 as the starting material. The synthetic strategy features a tandem Friedel-Crafts cyclization and lactonization, Vilsmeier-Haack and Julia-Kocienski olefination. This study laid the foundation for the synthesis of the parvistemonine A derivative and its biological activity research.

Strategies for the synthesis ofStemonaalkaloids: an update

“…The application of pyrrolic starting materials is emerging as an enabling tool for accessing the Stemona alkaloids. Indeed, at least 13 reports of the synthesis of stemoamide-, 13,15,18–20,23,47 a stenine-, 11,52 h , i and stichoneurine-type 76 structures from pyrrole precursors have been disclosed since 2009. This includes total syntheses of both pyrrole- and γ-lactam-containing 13,18,23,47 a ,76 natural products.…”

“…This includes total syntheses of both pyrrole- and γ-lactam-containing 13,18,23,47 a ,76 natural products. 11,15,19,20,52 h , i The latter molecules have been accessed directly from silyloxypyrroles and via the controlled oxidation of alkyl-substituted pyrroles. 114 Pyrroles can also serve as precursors to pyrrolidine-containing Stemona alkaloids in principle.…”

“…Reduction of olefin 7f through catalytic hydrogenation and α-methylation of the γ-lactone ring delivered alkaloid (±)- 1a . An enantioselective formal synthesis of bisdehydroneostemoninine 19 a and a racemic total synthesis of parvistemonine A ( 6p ) 19 b were also completed by these researchers. Racemic parvistemonine A ( 6p ) was also synthesised by Sugita and coworkers.…”

Unique assembly of carbonylpyridinium and chromene reveals mitochondrial thiol starvation under ferroptosis and novel ferroptosis inducer

“…Stemona alkaloids possess diverse structures and interesting biological activities. 30,31 In our previous work, [32][33][34][35] we synthesized several stemona alkaloids and their derivatives. To identify stemona alkaloids that induce ferroptosis, we performed CM-Mit-based uorescence assays to detect the effects of these stemona alkaloids on mitochondrial thiol levels.…”

Concise Diastereoselective Total Synthesis of (±)-Parvistemonine A

“…They obtained (±)-parvistemonine A in 11 steps and in 2.3% overall yield. 3 Our retrosynthetic analysis of (±)-1 is shown in Scheme 1. We planned to introduce the methyl group at the 1-position in the lactone ring at a late stage in the total synthesis by methylation of an ester enolate.…”