910219-34-0

Upstream product

• 76311-89-2 3-bromo-2,5-dihydrofuran-2-one 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 910219-41-9 (4-nitro-phenyl)-(2-triisopropylsilanyloxy-furan-3-yl)-methanol 
• 910219-39-5 phenyl-(2-triisopropylsilanyloxy-furan-3-yl)-methanol 
• 910219-40-8 (4-methoxy-phenyl)-(2-triisopropylsilanyloxy-furan-3-yl)-methanol 
• 910219-42-0 (3-chloro-phenyl)-(2-triisopropylsilanyloxy-furan-3-yl)-methanol 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Aglacins A, B, and E

An asymmetric photoenolization/Diels–Alder (PEDA) reaction between electron-rich 2-methylbenzaldehydes and unsaturated γ-lactones was developed to directly construct the basic tricyclic core of aryltetralin lactone lignans. This methodology enabled the first asymmetric total synthesis of aglacins A, B, and E and revision of the absolute configuration of these natural lignans. The strategy was also used to prepare the naturally occurring aryldihydronaphthalene-type lignans (?)-7,8-dihydroisojusticidin B and (+)-linoxepin in four and six steps, as well as 27 natural-product-like molecules containing a C8′ quaternary center. We believe that the synthetic aglacins and small-molecule library provide new opportunities to carry out the SAR studies of the podophyllotoxin family of natural products.

Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels–Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs

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 or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-γ-lactones. This occurred by a succession of (1) Heck coupling, (2) asymmetric dihydroxylation, (3) oxa-Pictet–Spengler cyclization, and (4) oxidation. The fifteen monomeric naphthoquinonopyrano-γ-lactone structures that we prepared resemble the natural product (–)-arizonin C1 or its C-5 epimer. Accordingly, they represent hexasubstituted naphthalenes likewise. The sixteenth naphthoquinonopyrano-γ-lactone that we synthesized is a kind of dimer. Its moieties are bridged differently than those in naturally occurring naphthoquinonopyrano-γ-lactone dimers.

Isotope-labeled methyl ketofuran, intermediate and method for preparing same

The invention discloses isotopically labeled methyl furanone, an intermediate and a preparation method of isotopically labeled methyl furanone. The invention provides isotopically labeled methyl furanone 6. The invention further provides a preparation method of isotopically labeled methyl furanone 6, and the preparation method comprises the following steps: performing removal of a hydroxy protecting group and isomerization reaction on a compound 20 in the presence of an acid. The method provided by the invention comprises short reaction steps, labeling loci are stable, are labeled on a common D ring of a strigolactone type compound family and are successfully butted with ABC rings of strigolactone type compounds to obtain a variety of isotopically labeled strigolactone type compounds with different isotopic abundances which are more than 99% respectively, and the isotopically labeled methyl furanone is applicable to wide substances, is used as an internal source standard matter for GC-MS and LC-MS/MS analysis and has high detection sensitivity and good accuracy, thereby having broad market application prospects.

Synthesis of stable isotopically labelled 3-methylfuran-2(5H)-one and the corresponding strigolactones

Conventional synthetic procedures of strigolactones (SLs) involve the independent synthesis of ring ABC and ring D, followed by a coupling of the two fragments. Here we prepared three kinds of stable, isotopically labelled D-ring analogues productively using a facile protocol. Then, a coupling of the D-rings to ring ABC produced three isotope-labelled SL derivatives. Moreover, (+)-D3-2′-epi-1A and (-)-ent-D3-2′-epi-1A with high enantiomeric purity were obtained via chiral resolution. We developed a convenient method to synthesize three kinds of stable, isotopically labelled D-ring analogues for subsequent production of isotope-labelled strigolactones. With this simple and universal method, three labelled 5-deoxystrigols (D3-1, 13C-1 and D313C-1) were synthesized.

Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B

Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.

Efficient synthesis of (E)-3-alkylidene-2(3H)-furanones from 3-(1-hydroxyalkyl)-2-silyloxyfurans

Several unsubstituted (E)-3-alkylmethylidene- and (E)-3-(arylmethylidene)- 2(3H)-furanones have been synthesized in highly stereoselective fashion by mesylation-elimination of 3-(1-hydoxyalkyl)-2-silyloxyfurans. The latter were prepared from 2-tri-isopropylsilyloxy-3-bromofuran by halogen-lithium exchange and reaction of the in situ generated 3-lithiated silyloxyfuran with aldehydes. Georg Thieme Verlag Stuttgart.