73376-38-2Relevant academic research and scientific papers
Enantiopure 2,3-Dihydro-4-pyridones as Synthetic Intermediates: A Concise Asymmetric Synthesis of (+)-Allopumiliotoxin 267A
Comins, Daniel L.,Huang, Shenlin,McArdle, Cheryl L.,Ingalls, Charles L.
, p. 469 - 471 (2001)
(Matrix Presented) A concise asymmetric synthesis of (+)-allopumiliotoxin 267A has been accomplished using an enantiopure dihydropyridone building block. The synthesis is highly stereoselective and requires 10 steps from readily available material.
Efficient construction of stereodefined α-alkylidene aza-cycloketones via β-amino-alkenyllithium: Straightforward and protection-free synthesis of allopumiliotoxin 267A
Wang, Bing,Zhong, Zheng,Lin, Guo-Qiang
body text, p. 2011 - 2014 (2009/09/06)
Intramolecular nucleophilic acyl substitution of highly functionalized /-amino-alkenyllithium species provided facile access to α-alkylidene aza-cycloketones with defined olefin geometry and rich structural diversity. A concise total synthesis of allopumi
Nickel-catalyzed preparation of bicyclic heterocycles: Total synthesis of (+)-allopumiliotoxin 267A, (+)-allopumiliotoxin 339A, and (+)-allopumiliotoxin 339B
Tang, Xiao-Qing,Montgomery, John
, p. 6950 - 6954 (2007/10/03)
A new method for the reductive cyclization of ynals involving a Ni(COD)2/PBu3 catalyst system to produce allylic alcohols was developed. The triethylsilane-mediated procedure allows preparation of functionally rich pyrrolizidine, ind
Enantioselective total syntheses of allopumiliotoxins 267A, 323B', and 339A. Application of iodide-promoted iminium ion-alkyne cyclizations for forming allopumiliotoxin A alkaloids
Caderas, Ristian,Lett, Renee,Overman, Larry E.,Rabinowitz, Michael H.,Robinson, Leslie A.,Sharp, Matthew J.,Zablocki, Jeffery
, p. 9073 - 9082 (2007/10/03)
A concise, stereocontrolled strategy for the total synthesis of allopumiliotoxin A alkaloids is described. A much improved second generation total synthesis of enantiopure (+)-allopumiliotoxin 267A (3) was accomplished in 10 steps and 11% overall yield from the commercially available oxazolidinone precursor of alcohol 32 and 17 steps and 4% overall yield from N-[(benzyloxy)carbonyl]-L-proline. The first synthesis of (+)-allopumiliotoxin 323B' (4) rigorously confirms the complete stereostructure of 4 and establishes that the major C(15) epimer isolated from dendrobatid frogs has the 15S configuration. The total synthesis of 4 was realized in 5 steps and 17% overall yield from alkyne 39 and aldehyde 20; the synthesis proceeded in 13 steps and 6% overall yield from (S)-2-methyl-1-penten-3-ol and 17 steps and 3.5% overall yield from N-[(benzyloxy)carbonyl]-L-proline, the precursors, respectively, of alkyne 39 and pyrrolidine aldehyde 20.The first total synthesis of allopumiliotoxin 339A (5) also confirmed the full stereostructure of this alkaloid. The synthesis of enantiopure 5 was achieved in 5 steps and 32% overall yield from alkyne 45 and pyrrolidine aldehyde 20; the synthesis proceeded in 17 steps and ~7% overall yield from N-[(benzyloxy)carbonyl]-L-proline and 16 steps and ~6% overall yield from the commercially available oxazolidinone precursor of 45. These syntheses provide the best illustrations to date of the substantial utility of iodide-promoted iminium ion-alkyne cyclizations for constructing highly functionalized nitrogen heterocycles.
Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/chromium(II)-mediated cyclization
Aoyagi, Sakae,Wang, Tzu-Chueh,Kibayashi, Chihiro
, p. 11393 - 11409 (2007/10/02)
Remarkably high regio- and stereoselective approaches for the syntheses of dendrobatid alkaloids (+)allopumiliotoxin 267A and 339A have been develop. As a model study for these alkaloids, we initially undertook intramolecular chromium(II)-mediated cycliza
The First Enantioselectice Total Syntheses of the Allopumiliotoxin A Alkaloids 267A and 339B
Goldstein, Steven W.,Overmann, Larry E.,Rabinowitz, Michael H.
, p. 1179 - 1190 (2007/10/02)
Short, highly stereocontrolled, asymmetric total syntheses of the title amphibian alkaloids are described.In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form.This short sequence proceeds in five laborato
