Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of a Tricyclic Core of Rameswaralide.

ABSTRACT: A tricyclic core containing a 5,7-fused bicyclic unit of rameswaralide was prepared starting from a 1,6-enyne. The synthetic sequence involved (i) ruthenium-catalyzed [5+2]-cycloaddition of 1,6-enyne, (ii) an acyl radical based approach to construct the lactone, and (iii) a regioselective installation of the conjugated double bond by a concomitant sulfenylation-dehydrosulfenylation sequence.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2976576 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of a Tricyclic Core of Rameswaralide.

Trost Barry M BM Nguyen Hien M HM Koradin Christopher C

Tetrahedron letters 20101201 48

A tricyclic core containing a 5,7-fused bicyclic unit of rameswaralide was prepared starting from a 1,6-enyne. The synthetic sequence involved (i) ruthenium-catalyzed [5+2]-cycloaddition of 1,6-enyne, (ii) an acyl radical based approach to construct the lactone, and (iii) a regioselective installation of the conjugated double bond by a concomitant sulfenylation-dehydrosulfenylation sequence. ...[more]

PMID: 21076637

Similar Datasets

Gold Catalysis-Facilitated Rapid Synthesis of the Daphnane/Tigliane Tricyclic Core.

Project description:A concise approach to synthesize the 5-7-6 tricyclic carbon skeleton of the daphnane/tigliane diterpene natural products has been accomplished via a sequential gold-catalyzed furan formation and furan-allene [4+3] cycloaddition. This work provides new avenues for rapid and diverted synthesis of the medicinally important daphnane/tigliane diterpenes and their unnatural analogues.

| S-EPMC5588696 | biostudies-literature

Development of a catalytic enantioselective synthesis of the guanacastepene and heptemerone tricyclic core.

Project description:For nearly two decades, synthetic chemists have been fascinated by the structural complexity and synthetic challenges afforded by the guanacastepene and heptemerone diterpenoids.Numerous synthetic approaches to these compounds have been reported, but to date the application of enantioselective catalysis to this problem has not been realized. Herein we report an enantioselective synthesis of an advanced intermediate corresponding to the tricyclic core common to the guanacastepenes and heptemerones. Highlights of this work include sequential Pd-catalyzed decarboxylative allylic alkylation reactions to generate the two all carbon quaternary stereocenters, the use of ring-closing metathesis to close the A ring in the presence of a distal allyl sidechain, and a region and diastereoselective oxidation of an trienol ether to introduce oxygenation on the A ring.

| S-EPMC6959853 | biostudies-literature

Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A-D.

Project description:Six regioisomers associated with the tricyclic core of thiaplakortones A-D have been synthesized. Reaction of 1H-indole-4,7-dione and 1-tosyl-1H-indole-4,7-dione with 2-aminoethanesulfinic acid afforded a regioisomeric series, which was subsequently deprotected and oxidized to yield the tricyclic core scaffolds present in the thiaplakortones. All compounds were fully characterized using NMR and MS data. A single crystal X-ray structure was obtained on one of the N-tosyl derivatives. All compounds were screened for in vitro antiplasmodial activity against chloroquine-sensitive (3D7) and multidrug-resistant (Dd2) Plasmodium falciparum parasite lines. Several analogues displayed potent inhibition of P. falciparum growth (IC50 < 500 nM) but only moderate selectivity for P. falciparum versus human neonatal foreskin fibroblast cells.

| S-EPMC4584354 | biostudies-literature

Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rh-Catalyzed [2+2+2] Cycloaddition.

Project description:An efficient approach to the tricyclic framework of FR901483 is described. The sequence features a [3, 3]-sigmatropic rearrangement of a cyanate into an isocyanate, followed by its subsequent asymmetric rhodium-catalyzed [2+2+2] cycloaddition with a terminal alkyne for the synthesis of the indolizidine core. The aza-tricyclic core is completed using an intramolecular benzoin reaction to close the last ring of the natural product. Through a model study of the key cycloaddition, we evaluated the impact of different substituents on the tether of the alkenyl isocyanate.

| S-EPMC4263289 | biostudies-literature

A synthesis of the ABC tricyclic core of the clionastatins serves to corroborate their proposed structures.

Project description:A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.

| S-EPMC3969099 | biostudies-literature

Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.

Project description:A facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of palau'amine and related pyrrole-imidazole alkaloids is described. Following gamma-lactam cleavage with concomitant epimerization at C12 of a previously reported tricycle, a facile intramolecular Mitsunobu reaction delivered the fully functionalized tricyclic core common to several members of the oroidin-derived alkaloids including palau'amine. An alternative cyclization of a related intermediate provides the tricyclic "aza-angular triquinane" core of the axinellamines.

| S-EPMC5548495 | biostudies-literature

Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

Project description:A novel approach to the tricyclic core of the Stemona alkaloids stemofoline and didehydrostemofoline has been discovered that features an intramolecular (3+2) dipolar cycloaddition of an unactivated carbon-carbon double bond with an azomethine ylide; the azomethine ylide was generated by an unprecedented reaction that occurred during a Swern oxidation of an ?-(N-cyanomethyl)-?-hydroxy ester. In separate experiments, the efficacy of introducing the requisite oxygen functionality at C(8) and the 1-butenyl side chain at C(3) was established.

| S-EPMC3079212 | biostudies-literature

Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

Project description:[reaction: see text] An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium-catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper-catalyzed enantioselective conjugate reduction of a beta-pyrrolyl enoate, and a regioselective Friedel-Crafts reaction. The synthesis of optically active and isomerically pure samples of (4aR)-myrmicarins 215A, 215B, and 217 in addition to their respective C4a-epimers is presented.

| S-EPMC2992882 | biostudies-literature

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

Synthesis of a library of tricyclic azepinoisoindolinones.

Project description:Hydrozirconation of 1-hexyne, the addition to in situ prepared N-acyliminium species, and ring-closing metathesis (RCM) were key steps in the preparation of a tricyclic isoindolinone scaffold. An unusual alkene isomerization process during the RCM was identified and studied in some detail. Chemical diversification for library synthesis was achieved by a subsequent alkene epoxidation and zinc-mediated aminolysis reaction. The resulting library products provided selective hits among a large number of high-throughput screens reported in PubChem, thus illustrating the utility of the novel scaffold.

| S-EPMC3458725 | biostudies-other

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