893442-84-7Relevant academic research and scientific papers
A strategy for complex dimer formation when biomimicry fails: Total synthesis of ten coccinellid alkaloids
Sherwood, Trevor C.,Trotta, Adam H.,Snyder, Scott A.
, p. 9743 - 9753 (2014/07/22)
Although dimeric natural products can often be synthesized in the laboratory by directly merging advanced monomers, these approaches sometimes fail, leading instead to non-natural architectures via incorrect unions. Such a situation arose during our studies of the coccinellid alkaloids, when attempts to directly dimerize Natures presumed monomeric precursors in a putative biomimetic sequence afforded only a non-natural analogue through improper regiocontrol. Herein, we outline a unique strategy for dimer formation that obviates these difficulties, one which rapidly constructs the coccinellid dimers psylloborine A and isopsylloborine A through a terminating sequence of two reaction cascades that generate five bonds, five rings, and four stereocenters. In addition, a common synthetic intermediate is identified which allows for the rapid, asymmetric formal or complete total syntheses of eight monomeric members of the class.
Synthesis of an optically pure synthetic intermediate of aloperine from a yeast-reductive product
Yamauchi, Satoshi,Omi, Yasushi
, p. 1589 - 1594 (2008/02/02)
Optically pure (S)- and (R)-vinylpiperidine 2 and (S)-and (A)-(hydroxyethyl)piperidine 3, which were key intermediates for the synthesis of aloperine, were synthesized from yeast-reductive products.
