Browse
Submit Data
Databases
API
Help

Dataset Information

27 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Studies Directed toward the Stereoselective Synthesis of Cytospolide E.

ABSTRACT: Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8-epi-9-epi-cytospolide E following the regioselective formation of a 10-membered macrocycle over a 9-membered macrocycle.

SUBMITTER: Chatterjee S

PROVIDER: S-EPMC6641448 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Studies Directed toward the Stereoselective Synthesis of Cytospolide E.

Chatterjee Shamba S Kuilya Tapan Kumar TK Goswami Rajib Kumar RK

ACS omega 20180125 1

Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8-<i>epi</i>-9-<i>epi</i>-cytosp ...[more]

PMID: 31457947

Similar Datasets

Studies directed toward the synthesis of the massileunicellins. 2.

Project description:The fully substituted hydroisobenzofuran core of the massileunicellins containing 8 contiguous stereocenters was prepared in 12 steps from (S)-(+)-carvone. Noteworthy elements of the synthesis include a one-step oxidative rearrangement/epoxidation, a novel stereoselective directed reduction of a keto diol, and a directed hydrogenation of a congested tetrasubstituted alkene.

| S-EPMC3111956 | biostudies-literature

Studies toward the first stereoselective total synthesis of (±)-quinolizidine 195C and other transformations.

Project description:Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin extracts of the Madagascan frog Mantella betsileo. Since the spectral data of the synthetic and natural products differed significantly, the true structure of (±)-quinolizidine 195C remains uncertain.

| S-EPMC6269906 | biostudies-other

Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Project description:An enantioselective synthesis of the C(1)-C(15) segment of the marine natural product amphidinolide C has been accomplished by a route that includes a stereoselective boron-Wittig reaction to furnish a trisubstituted alkenylboronate. In addition, the route employs enantioselective alkene diboration to install the C(6) hydroxyl group which undergoes intramolecular conjugate addition to establish a tetrahydrofuran ring. Lastly, a catalytic Suzuki-Miyaura cross-coupling is accomplished to construct the C(9)-C(10) bond.

| S-EPMC7982962 | biostudies-literature

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates.

Project description:While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxiran-2-yl)chroman, which have been used as late-stage intermediates for the asymmetric synthesis of the antihypertensive drug (S,R,R,R)-nebivolol. Noteworthy is that a large number of racemic and asymmetric syntheses of nebivolol and their intermediates have been described in the literature, however, the Sharpless asymmetric dihydroxylation has never been employed as the sole source of chirality for this purpose.

| S-EPMC5372751 | biostudies-literature

Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Project description:A method for a directed stereoselective guanidinylation of alkenes is described. The guanidine unit can be delivered as an intact fragment by a hydroxy or carboxy group, usually with a high level of stereocontrol. After the guanidine delivery, the directing group can be cleaved under exceptionally mild conditions, typically by alcoholysis in the presence of acetic acid. Broad functional group tolerance and mild reaction conditions for the cycloguanidilation suggest applications in medicinal chemistry and natural products synthesis.

| S-EPMC5598158 | biostudies-literature

Regio- and stereoselective synthesis of fluoroalkenes by directed Au(I) catalysis.

Project description:Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved. In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.

| S-EPMC2753819 | biostudies-literature

Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition.

Project description:The tetracyclic core of the diterpene bielschowskysin has been prepared as a single enantiomer via a stereoselective intramolecular [2+2] photocycloaddition of 5-alkylidene-2(5H)-furanone 3.

| S-EPMC2527052 | biostudies-literature

An alkoxide-directed alkyne-allene cross-coupling for stereoselective synthesis of 1,4-dienes.

Project description:A titanium alkoxide-mediated convergent coupling between internal alkynes and allenes is described for the regio- and stereocontrolled synthesis of substituted acyclic 1,4-dienes.

| S-EPMC4319186 | biostudies-literature

Studies on the synthesis of durhamycin A: stereoselective synthesis of a model aglycone.

Project description:A stereoselective synthesis of the model aglycone corresponding to the anti-HIV aureolic acids durhamycins A (1) and B (2) is described.

| S-EPMC2626543 | biostudies-literature

Studies toward the synthesis of maoecrystal V.

Project description:An approach toward the synthesis of maoecrystal V is described. The synthetic strategy for this approach was designed to address unique challenges posed by the strained tetrahydrofuran ring at the center of the target structure.

| S-EPMC3373731 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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