57236-37-0

Upstream product

• 54274-81-6 4,5,6-tri-O-acetylpentenomycin I 
• 86531-77-3 (2S,3S,4R)-4-benzyloxy-2-benzyloxymethyl-2,3-dihydroxycyclopentan-1-one 
• 80963-24-2 6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene 
• 68241-78-1 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene 
• 10481-34-2 2-bromo-2-cyclopenten-1-one 
• 68882-71-3 2-(hydroxymethyl)cyclopent-2-enone 
• 68882-72-4 2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone 
• 652157-41-0 (-)-(3S,7R)-7-hydroxy-1-oxaspiro[2.4]hept-5-en-4-one 
• 86531-78-4 (2S,3S,4R)-2-hydroxymethyl-2,3,4-trihydroxycyclopentan-1-one 
• 1042926-20-4 (2S,5S,6S,5'R)-5'-hydroxy-2'-oxospiropent-3'-ene-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane 
• 652157-40-9 (-)-(4R)-4-hydroxy-5-methylene-2-cyclopentenone 
• 1431731-79-1 (3aR,6S,6aS)-3a-((tert-butyldimethylsilyloxy)methyl)-6-isopropoxy-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 

Relevant academic research and scientific papers

A facile synthesis of (+)/(?)-pentenomycin I and analogs, and their antimicrobial evaluation

This study reported a stereoselective synthesis of (+)/(+)-pentenomycin I in 4–5 steps through regioselective silylation, optical resolution and dihydroxylation, followed by an olefin formation, from a known racemic cyclopentenone prepared from 2-deoxy-D-

Synthesis of (±) epipentenomycin I and III

A synthesis of (±) epipentenomycin I and III is reported from a regioselective epoxidation of racemic 3-hydroxy- and 3-acetoxy-2-methylene-4-cyclopentenone, respectively, with dimethyldioxirane followed by hydrolytic ring-opening of the resulting epoxide.

Total synthesis of (±)-pentenomycin

A concise stereoselective route to (±)-pentenomycin 1 in 33% overall yield starting from the readily accessible Diels-Alder adduct 4 is reported. The key reaction involves decarbonylation of β-methoxy-α,β-unsaturated aldehyde 8 obtained from β-hydroxy-dimethylketal 6.

Chemo-enzymatic synthesis of (-)-epipentenomycin I

A chemo-enzymatic synthesis of (-)-epipentenomycin I is reported using a lipase-catalysed kinetic resolution of the racemic pentacyclic alcohol 8. Flash vacuum pyroloysis of (-)-8 so obtained gave (-)-(4R)-4-hydroxy-5-methylene-2- cyclopentenone. Epoxidation of this compound with dimethyldioxirane followed by hydrolytic ring-opening of the resulting epoxide gave (-)-epipentenomycin I.

METHOD OF PRODUCING PENTENOMYCIN DERIVATIVES

PROBLEM TO BE SOLVED: To provide a high-yield, simple method of producing optically active pentenomycin and derivatives thereof. SOLUTION: There is provided a method of producing a pentenomycin derivative represented by the formula (I) in the figure, where Ra and Rb each represent a hydrogen atom or acyl group. The method of producing a compound represented by the formula (I) comprises converting a hydroxymethyl group protected with a silyl group or the like at the 5-position of a cyclopentenone ring into a hydroxymethyl group or acyloxymethyl group. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

A common and versatile synthetic route to (-) and (+) pentenomycin I, (+) halopentenomycin i and dehydropentenomycin

A versatile and stereoselective total synthesis of (+) and (-) pentenomycin I, (+) halopentenomycins I and dehydropentenomycin from a common chiral polyhydroxylated cyclopentene through oxidation and protection/deprotection has been described. Stereoselec

Synthesis of (+)/(-) pentenomycins via Me2AlCl induced cascade reaction

An efficient approach for the synthesis of (+) pentenomycin and (-) pentenomycin from d-ribose and d-mannose, respectively, is described using Tebbe olefination of lactones 9 and 7 followed by Me2AlCl induced disfavoured 5-(enol-endo)-exo-trig

Asymmetric synthesis of pentenomycin I, epipentenomycin I, and their analogs

The synthetic utility of the intramolecular acylation of α-sulfinyl carbanions as an efficient and general synthetic approach for the preparation of (-)-pentenomycin I (1) and (-)-epipentenomycin I (5) and their enantiomers (ent-1 and ent-5), starting fro

An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.

Vinyl sulfoxides as stereochemical controllers in intermolecular Pauson-Khand reactions: Applications to the enantioselective synthesis of natural cyclopentanoids

The use of sulfoxides as chiral auxiliaries in asymmetric intermolecular Pauson-Khand reactions is described. After screening a wide variety of substituents on the sulfur atom in α,β-unsaturated sulfoxides, the readily available o-(N,N-dimethylamino)phenyl vinyl sulfoxide (1i) has proved to be highly reactive with substituted terminal alkynes under N-oxide-promoted conditions (CH3CN, 0°C). In addition, these Pauson-Khand reactions occurred with complete regioselectivity and very high diastereoselectivity (de = 86→96%, (S,RS) diastereomer). Experimental studies suggest that the high reactivity exhibited by the vinyl sulfoxide 1i relies on the ability of the amine group to act as a soft ligand on the alkyne dicobalt complex prior to the generation of the cobaltacycle intermediate. On the other hand, both theoretical and experimental studies show that the high stereoselectivity of the process is due to the easy thermodynamic epimerization at the C5 center in the resulting 5-sulfinyl-2- cyclopentenone adducts. When it is taken into account that the known asymmetric intermolecular Pauson-Khand reactions are limited to the use of highly reactive bicyclic alkenes, mainly norbornene and norbornadiene, this novel procedure constitutes the first asymmetric version with unstrained acyclic alkenes. As a demonstration of the synthetic interest of this sulfoxide-based methodology in the enantioselective preparation of stereochemically complex cyclopentanoids, we have developed very short and efficient syntheses of the antibiotic (-)-pentenomycin I and the (-)-aminocyclopentitol moiety of a hopane triterpenoid.