Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition.

ABSTRACT: [structure: see text]. An efficient, enantioselective approach to the hetisine class of the C(20)-diterpenoid alkaloids is described. The strategy involves an intramolecular oxidopyridinium dipolar cycloaddition as the key transformation, in which simultaneous formation of the C5-C6 and C10-C20 bonds in the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core of the hetisine alkaloids is effected.

SUBMITTER: Peese KM

PROVIDER: S-EPMC2593868 | biostudies-other | 2005 Jul

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition.

Peese Kevin M KM Gin David Y DY

Organic letters 20050701 15

[structure: see text]. An efficient, enantioselective approach to the hetisine class of the C(20)-diterpenoid alkaloids is described. The strategy involves an intramolecular oxidopyridinium dipolar cycloaddition as the key transformation, in which simultaneous formation of the C5-C6 and C10-C20 bonds in the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core of the hetisine alkaloids is effected. ...[more]

PMID: 16018651

Similar Datasets

Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids.

Project description:An intramolecular non-stabilized azomethine ylide dipolar cycloaddition was applied toward the first non-racemic synthesis of the fully-oxygenated bridged pyrrolizidine core (45) of (+)-stemofoline (1) in eleven steps from a commercially available starting material.

| S-EPMC2352155 | biostudies-literature

8-Phenyl-10-oxa-8-aza-tricyclo-[4.3.0.1]decane-7,9-dione.

Project description:The reaction of aniline with norcantharidin produced the imide title compound, C(14)H(13)NO(3), which shows no significant hydrogen bonds in the crystal structure. The dihedral angle between the phenyl and pyrrolidine rings is 48.48?(6)°.

| S-EPMC2968178 | biostudies-literature

4-(3,5-Dioxo-10-oxa-4-aza-tricyclo-[5.2.1.0]decan-4-yl)-10-oxa-4-aza-tricyclo-[5.2.1.0]decane-3,5-dione.

Project description:In the title compound, C(16)H(16)N(2)O(6), the dihedral angle between the two pyrrolidine rings is 79.38?(14)°.

| S-EPMC3275059 | biostudies-literature

Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.

Project description:An organocatalytic strategy for the synthesis of tetrasubstituted pyrrolidines with monoactivated azomethine ylides in high enantiomeric excess and excellent exo/endo selectivity is presented. The key to success is the intramolecular activation via hydrogen bonding through an o-hydroxy group, which allows the dipolar cycloaddition to take place in the presence of azomethine ylides bearing only one activating group. The intramolecular hydrogen bond in the azomethine ylide and the intermolecular hydrogen bond with the catalyst have been demonstrated by DFT calculations and mechanistic proofs to be crucial for the reaction to proceed.

| S-EPMC5839603 | biostudies-literature

Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes.

Project description:Enantioenriched allenylsilanes are used in three-component propargylation reactions with aldehydes and silyl ethers to form syn-homopropargylic ethers that contain an imbedded azide. These materials then undergo thermally induced intramolecular 1,3-dipolar cycloaddition reactions, resulting in unique fused ring systems containing 1,2,3-triazoles. The ability to modify all three components of the reaction allows for expedient access to compounds containing significant structural and stereochemical variation.

| S-EPMC3164318 | biostudies-literature

Intramolecular diels-alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles.

Project description:Full details of a systematic exploration of the intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles are disclosed in which the scope and utility of the reaction are defined.

| S-EPMC2587417 | biostudies-literature

A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine.

Project description:An enantioselective route to the C,D-bicycle of massadine is reported. Enantiopure intermediates were generated by a single stereoselective reduction using the Corey-Bakshi-Shibata reagent. This initial stereoinduction was translated into the five contiguous stereocenters of the massadine D-ring by a synthetic route that features a diastereoselective and stereospecific Ireland-Claisen rearrangement of a trianionic enolate followed by a diastereoselective nitrone dipolar cycloaddition of a highly electron-poor oxime.

| S-EPMC6674976 | biostudies-literature

exo-4-[(1H-Benzimidazol-2-yl)meth-yl]-10-oxa-4-aza-tricyclo-[5.2.1.0]decane-3,5-dione.

Project description:In the title compound, C(16)H(15)N(3)O(3), the dihedral angle between the approximately planar benzimidazolyl group (r.m.s. deviation = 0.010?Å) and the pyrrolidine ring is 78.20?(6)°. The C-C-N bond angle of the bridging CH(2) group is 112.14?(16)°. In the crystal, mol-ecules are linked via N-H?N hydrogen bonds, forming infinite chains parallel to [101] and [10[Formula: see text]].

| S-EPMC3213433 | biostudies-literature

Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition.

Project description:Sterically shielded nitroxides of the pyrrolidine series have shown the highest resistance to reduction. Here we report the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were studied and compared to those of previously published (1S,2R,3'S,4'S,5'S,2?R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2'-(3',4'-di-tert-butoxy)pyrrolidine-5',1?-(2?-hydroxymethyl)cyclopentane]-1'-oxyl (1).

| S-EPMC6720653 | biostudies-literature

An intramolecular relay catalysis strategy for Knoevenagel condensation and 1,3-dipolar cycloaddition domino reactions.

Project description:A relay catalysis strategy was established by using a bifunctional catalyst which was prepared by immobilization of organic chains containing secondary amine and Cu(ii) complex onto silica-coated nano-Fe3O4. The simply prepared nanoparticles acted as efficient, intramolecular relays and magnetically recyclable base-metal bifunctional catalysts for Knoevenagel condensation and 1,3-dipolar cycloaddition domino reactions to prepare 5-substituted 1H-tetrazoles with excellent yields.

| S-EPMC9073340 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data