38211-56-2Relevant articles and documents
2-Dehydrococcinelline, a new defensive alkaloid from the ladybird beetle Anatis ocellata (Coccinellidae)
Lebrun,Braekman,Daloze,Pasteels
, p. 1148 - 1149 (1997)
2-Dehydrococcinelline (6), a novel coccinellid defensive alkaloid, has been isolated from the European ladybird Anatis ocellata. Its structure was established by spectroscopic methods and confirmed by chemical correlation with precoccinelline (1).
A strategy for complex dimer formation when biomimicry fails: Total synthesis of ten coccinellid alkaloids
Sherwood, Trevor C.,Trotta, Adam H.,Snyder, Scott A.
supporting information, 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.
Stereodivergent total syntheses of precoccinelline, hippodamine, coccinelline, and convergine
Gerasyuto, Aleksey I.,Hsung, Richard P.
, p. 4899 - 4902 (2007/10/03)
(Chemical Equation Presented) A stereodivergent approach toward total syntheses of Coccinellidae defensive alkaloids is described. These syntheses feature a highly diastereoselective intramolecular aza-[3 + 3] annulation strategy, which represents a de no
Combining two-directional synthesis and tandem reactions:? an efficient strategy for the total syntheses of (±)-hippodamine and (±)-epi-hippodamine
Rejzek, Martin,Stockman, Robert A.,Hughes, David L.
, p. 73 - 83 (2007/10/03)
Two-directional total stereoselective syntheses of (±)-hippodamine and (±)-epi-hippodamine, utilising a tandem deprotection/intramolecular double Michael addition sequence as the key step, are presented.
A new stereoselective synthesis of ladybug defence alkaloid precoccinelline
Yue,Nicolay,Royer,Husson
, p. 3139 - 3148 (2007/10/02)
We have accomplished a new stereoselective synthesis of precoccinelline 1 in six steps from the chiral synthon 6 with a overall yield of 31%. The main feature of this synthesis is the asymmetric synthesis of the trans 2,6-keto- acetal piperidine 14 which
Nitrone Cycloaddition-based Entry to the Coccinelline Alkaloid Skeleton: Synthesis of (+/-)-epi-Hippodamine
Adams, David R.,Carruthers, William,Crowley, Patrick J.
, p. 1261 - 1263 (2007/10/02)
Synthesis of intermediate 13 possessing the perhydropyridoquinolizine skeleton of the coccinelline alkaloids and conversion to epi-hippodamine 20 was accomplished with stereochemical control arising from a key cycloaddition reaction of nitrone 2 with ethyl hexa-3,5-dienoate.
Stereo- and Regioselective Total Synthesis of the Hydropyridoquinolizine Ladybug Defensive Alkaloids
Mueller, Richard H.,Thompson, Mark E.,DiPardo, Robert M.
, p. 2217 - 2231 (2007/10/02)
The stereo- and regioselective syntheses of the ladybug defensive alkaloids coccinelline (1), precoccinelline (2), (+/-)-hippodamine (3), (+/-)-convergine (4), (+/-)-hippocasine (5), (+/-)-hippocasine oxide (6), myrrhine (7), (+/-)-propyleine (8), and (+/-)-isopropyleine (9) are described starting from perhydroboraphenalene.
SYNTHESIS OF THE LADYBUG DEFENSIVE AGENTS (+-)-HIPPODAMINE, (+-)-CONVERGINE, (+-)-HIPPOCASINE AND (+-)-HIPPOCASINE OXIDE
Mueller, Richard H.,Thompson, Mark E.
, p. 1093 - 1096 (2007/10/02)
The total syntheses of the ladybug defensive agents (+-)-hippoidamine, (+-)-convergine, (+-)-hippocasine, and (+-)-hippocasine oxide are described starting from perhydroboraphenalene.
