A divergent enantioselective strategy for the synthesis of griseusins.
@article{Zhang2015ADE, title={A divergent enantioselective strategy for the synthesis of griseusins.}, author={Yinan Zhang and Qing Ye and Xiachang Wang and Qing-Bai She and Jon S. Thorson}, journal={Angewandte Chemie}, year={2015}, volume={54 38}, pages={ 11219-22 } }
The first enantioselective total synthesis of griseusin A, griseusin C, 4'-deacetyl-griseusin A, and two non-native counterparts in 11-14 steps is reported. This strategy highlights a key hydroxy-directed CH olefination of 1-methylene isochroman with an α,β-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cyclization to afford the signature tetrahydro-spiropyran ring. Colorectal cancer cell cytotoxicities of the final products highlight the impact of the…
18 Citations
Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans.
- ChemistryOrganic letters
- 2016
Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, γ-lactones, and isobenzofuranones in 44-82%…
Stereoselective Total Synthesis of the Dimeric Naphthoquinonopyrano-γ-lactone (-)-Crisamicin A: Introducing the Dimerization Site by a Late-Stage Hartwig Borylation.
- ChemistryOrganic letters
- 2020
The first stereoselective total synthesis of the dimeric naphthoquinonopyrano-γ-lactone (-)-crisamicin A was realized and led to a binaphthohydroquinon-5-yl.
First Stereoselective Total Synthesis of a Dimeric Naphthoquinonopyrano-γ-lactone: (+)-γ-Actinorhodin.
- ChemistryAngewandte Chemie
- 2017
This work has accomplished the first total synthesis of an isomerically pure naphthoquinonopyrano-γ-lactone dimer, γ-actinorhodin, in eleven steps, and established the absolute configuration of the target compound, which was established in an asymmetric Sharpless dihydroxylation of a β,γ-unsaturated ester.
Enaminones as Synthons for a Directed C-H Functionalization: Rh(III) -Catalyzed Synthesis of Naphthalenes.
- ChemistryAngewandte Chemie
- 2016
Proof-of-concept protocols have been developed for the Rh(III) -catalyzed synthesis of naphthalenes, based on the coupling of enaminones with either alkynes or α-diazo-β-ketoesters.
Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels–Alder Additions: Regio‐ and Stereocontrolled Synthesis of Arizonin C1 Analogs
- Chemistry
- 2017
3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels-Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free and a…
Nonracemic γ‐Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters
- Chemistry
- 2016
Since Sharpless' discovery of the asymmetric dihydroxylation of C=C double bonds in the late 1980s this reaction has become a powerful tool of synthetic organic chemistry. As a consequence, this…
Regioselective synthesis of naphthoquinone/naphthoquinol-carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity.
- Chemistry, BiologyOrganic & biomolecular chemistry
- 2016
The in vitro cytotoxic activity of the synthetic naphthoquinone/naphthonol-carbohydrate hybrids were evaluated against the human cervical cancer cell line (HeLa), and a few of them were found to exhibit potent anticancer activity against the cell line.
Total Synthesis of Aryl C-Glycoside Natural Products: Strategies and Tactics.
- ChemistryChemical reviews
- 2018
The aryl C-glycoside structure is, among the plenty of biologically active natural products, one of the distinct motifs embedded, and the synthetic strategies and tactics employed in the total synthesis of this class of natural products.
Recent progress in the isolation, bioactivity, biosynthesis, and total synthesis of natural spiroketals.
- Chemistry, BiologyNatural product reports
- 2018
This review focuses on the overview of the isolation, bioactivity, biosynthesis and total synthesis of spiroketals from 2011 to July 2017.
References
SHOWING 1-10 OF 46 REFERENCES
TESOTf-induced rearrangement of quinols. Efficient construction of the fully functionalized carbon skeleton of the griseusins by a divergent-reconvergent approach.
- ChemistryOrganic letters
- 2006
The "reverse polarity" or "umpolung" strategy for the total synthesis of aryl C-glycosides was developed in the context of the antibiotic (-)-griseusin B and was converted to the same advanced model intermediate that contains the complete carbon skeleton and the functional group pattern of the griseusins.
Synthesis of Analogues of Griseusin A
- Chemistry
- 1999
The synthesis of pyranonaphthoquinone-spiroacetals (3 and 4), which are synthetic analogues of the pyranonaphthoquinone antibiotic griseusin A (1) is reported. The oxygenated substituents on the…
Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.
- ChemistryOrganic letters
- 2009
A systematic stereocontrolled synthesis of benzannulated spiroketals has been developed, using kinetic spirocyclization reactions of glycal epoxides, leading to a new AcOH-induced cyclization and…
A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.
- ChemistryOrganic letters
- 2013
An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.
Solvent-Dependent Divergent Functions of Sc(OTf)3 in Stereoselective Epoxide-Opening Spiroketalizations
- ChemistryOrganic letters
- 2014
A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)3-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains to accommodate a variety of aryl substituents and ring sizes and provide stereochemically diverse spiro ketals.
Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle
- Chemistry
- 2014
A protocol for palladium-catalyzed ortho C(sp2)–H alkenylation via a rarely reported seven-membered palladacycle with oxalyl amide as a directing group was reported. The range of olefins was the…
Direct Aerobic α, β-Dehydrogenation of Aldehydes and Ketones with a Pd(TFA)(2)/4,5-Diazafluorenone Catalyst().
- ChemistryChemical science
- 2012
A new Pd(TFA)(2)/4,5-diazafluorenone dehydrogenation catalyst that overcomes key limitations of previous catalyst systems is described, which includes successful reactivity with pharmaceutically important cyclopentanone and flavanone substrates, as well as acyclic ketones.
Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones.
- ChemistryJournal of the American Chemical Society
- 2011
Pd(DMSO)(2)(TFA)(2) is reported to be a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O(2) as the oxidant.
A titanium naphtholate approach for the synthesis of analogues of griseusin A
- Chemistry
- 2000
The synthesis of analogues of the spiroketal-containing pyranonaphthoquinone antibiotic griseusin A 1 is described. The key disconnection focused on hydroxyalkylation of naphthol 21 with aldehyde 12.…