Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.

ABSTRACT: Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC3345064 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.

Crimmins Michael T MT Dechert Anne-Marie R AM

Organic letters 20120418 9

Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones. ...[more]

PMID: 22512249

Similar Datasets

Enantioselective syntheses of the proposed structures of cytotoxic macrolides iriomoteolide-1a and -1b.

Project description:Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

| S-EPMC2920059 | biostudies-literature

Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide.

Project description:Both epimers at C-21 in the proposed structure of (+)-callyspongiolide have been synthesized in a convergent and enantioselective manner. The 14-membered macrolide with a sensitive C2-C3 cis-olefin functionality was installed by a Yamaguchi macrolactonization of hydroxyl alkynoic acid followed by hydrogenation over Lindlar's catalyst. The C5 methyl stereocenter was constructed by a ring-closing olefin metathesis followed by addition of methyl cuprate to an α,β-unsaturated δ-lactone. Other key reactions are chiral Corey-Bakshi-Shibata (CBS) reduction and Sonogashira coupling to conjoin the macrocyclic core and side chain.

| S-EPMC6037179 | biostudies-literature

Enantioselective synthesis of the C1-C11 fragment of tedanolide C.

Project description:A convergent synthesis of the protected C(1)-C(11) fragment 6 of the targeted enantiomer of tedanolide C is described. The key step of the synthesis is the Felkin-Ahn addition of vinyl iodide 7 to aldehyde 8 that proceeds in 80% yield with 4:1 diastereoselectivity.

| S-EPMC3539184 | biostudies-literature

Synthesis of a C1-C23 fragment of the archazolids and evidence for V-ATPase but not COX inhibitory activity.

Project description:A convergent synthesis of a C1-C23 fragment of the archazolids has been completed based on a high yielding Stille coupling to costruct the substituted Z,Z,E-conjugated triene. After removal of the protecting groups, the resulting tetrol exhibited evidence for inhibition of the vacuolar-type ATPase (V-ATPase) but not cyclooxygenase (COX) inhibitory activity.

| S-EPMC6779165 | biostudies-literature

Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Project description:The C1-C6 region of the potent cytotoxic agent psymberin has been synthesized. The key transformations of the synthesis are an auxiliary-controlled addition of a Sn(II)-glycolate enolate to an aldehyde to yield the anti aldol product and transforming the primary alcohol into a terminal olefin utilizing organoselenium chemistry.

| S-EPMC4124943 | biostudies-literature

Evolution of a strategy for the synthesis of structurally complex batzelladine alkaloids. Enantioselective total synthesis of the proposed structure of batzelladine F and structural revision.

Project description:Stereoselective synthesis of octahydro-5,6,6a-triazaacenaphthalenes 29 and 34 having the anti-relationship of the angular hydrogens flanking the pyrrolidine nitrogen confirmed suspicions that the relative configuration of the left-hand tricyclic guanidine fragment of batzelladine F should be revised to have the syn relationship of these hydrogens. Several strategies were examined for coupling tricyclic guanidine fragments to prepare potential structures for batzelladine F. Eventually, a convergent synthesis strategy was devised, whose central step was a fragment-coupling tethered-Biginelli reaction (Scheme 17). Using this approach we synthesized four potential structures of batzelladine F, 35-38. None of these compounds, nor their enantiomers, were identical to natural batzelladine F. Reinvestigation of mass spectra of natural batzelladine F, and fragments 88 and 89 obtained upon saponification of batzelladine F, demonstrated that the originally proposed connectivity of this alkaloid was also incorrect. The revised connectivity, 90, of natural batzelladine F depicted in Scheme 21 is proposed.

| S-EPMC2535801 | biostudies-literature

Total synthesis of the proposed structure of briarellin J.

Project description:The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

| S-EPMC2966518 | biostudies-literature

Total Synthesis of the Proposed Structure of Paraphaeosphaeride C.

Project description:Paraphaeosphaeride C is a demethoxy derivative of phaeosphaeride A and exhibits STAT3 inhibitory activity. Our previous papers reported the total synthesis of phaeosphaeride A using a diastereoselective vinyl anion aldol reaction as the key step to construct the dihydropyran ring. In this work, the first total synthesis of the proposed structure of paraphaeosphaeride C was achieved via a similar synthetic strategy. The synthetic compound was characterized through extensive nuclear magnetic resonance (NMR) analysis but the 1H and 13C-NMR data for this compound did not correspond to those reported in the literature for paraphaeosphaeride C.

| S-EPMC6930451 | biostudies-literature

Total synthesis of the proposed structure of astakolactin.

Project description:The first total synthesis of the proposed structure of astakolactin, a sesterterpene metabolite isolated from the marine sponge Cacospongia scalaris, has been achieved, mainly featuring Johnson-Claisen rearrangement, asymmetric Mukaiyama aldol reaction and MNBA-mediated lactonization.

| S-EPMC4222296 | biostudies-other

Catalytic Enantioselective Synthesis of C1 - and C2 -Symmetric Spirobiindanones through Counterion-Directed Enolate C-Acylation.

Project description:A catalytic enantioselective route to C1 - and C2 -symmetric 2,2'-spirobiindanones has been realized through an intramolecular enolate C-acylation. This reaction employs a chiral ammonium counterion to direct the acylation of an in?situ generated ketone enolate with a pentafluorophenyl ester. This reaction constitutes the first example of a direct catalytic enantioselective C-acylation of a ketone and provides an efficient and highly enantioselective route to axially chiral spirobiindanediones. These products can be diastereoselectively derivatized, offering access to a range of functionalized spirocyclic architectures.

| S-EPMC5113699 | biostudies-other

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