419568-67-5

Usage

Uses

Different sources of media describe the Uses of 419568-67-5 differently. You can refer to the following data:
1. An antitumor natural product
2. An antitumor natural product.

Upstream product

• 1064181-40-3 C₃₇H₅₀O₇Si 
• 133908-85-7 L-ribono-1,4-lactone 
• 1451265-62-5 2-((3R,4R,E)-3,4-dihydroxy-4-((2R,3R)-3-methyloxiran-2-yl)but-1-enyl)-6-methoxybenzyl acetate 
• 1451265-61-4 2-((S,E)-4-hydroxy-4-((2R,3R)-3-methyloxiran-2-yl)-3-oxobut-1-enyl)-6-methoxybenzyl acetate 
• 81625-30-1 2-(ethoxycarbonyl)-3-methoxybenzyl chloride 
• 1392482-34-6 tert-butyl(2-(chloromethyl)-6-methoxybenzyloxy)dimethylsilane 
• 1392482-33-5 (2-(chloromethyl)-6-methoxyphenyl)methanol 
• 1356005-06-5 (3aS,4S,6S,6aS)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde 
• 1392482-29-9 diethyl 2-((tert-butyldimethylsilyloxy)methyl)-3-methoxybenzylphosphonate 
• 1352945-24-4 (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole 
• 75467-36-6 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 

Relevant academic research and scientific papers

Stereocontrolled Nucleophilic Addition to Five-Membered Oxocarbenium Ions Directed by the Protecting Groups. Application to the Total Synthesis of (+)-Varitriol and of Two Diastereoisomers Thereof

A stereodivergent C-glycosidation of carbohydrate-derived lactones can be mediated by the protecting groups and applied to the total synthesis of (+)-varitriol and of two diastereoisomers thereof, which represent an unprecedent use of the protecting groups in the synthesis of a naturally occurring compound. In particular, the stereoselective nucleophile attack for 2,3-trans-substituted five-membered ring oxocarbenium ions is strongly influenced by the presence of aromatic rings in the protecting groups. According to quantum chemical calculations, the stereoselectvity depends on the π-π interactions between the aromatic ring of the C-2 protecting group with the exocyclic triple bond and the oxocarbenium ion. These interactions account for the stabilization of the conformer in which the C-2 and C-3 substituents adopt pseudoaxial orientations. When protecting groups do not contain an aromatic ring, the sterochemical outcome is dictated by stereoelectronic factors established by the Woerpel's model. Based on these findings, a concise total synthesis of the natural product (+)-varitriol and of two diastereoisomers was acomplished.

Total synthesis of varitriol, varioxirane, and enantiomer of the proposed biosynthetic precursor

The first stereoselective total synthesis of varioxirane was accomplished, and the proposed biosynthetic pathway was supported by converting varioxirane to (+)-varitriol. The first total synthesis of enantiomer of the proposed biosynthetic precursor, (1E,3S,4R,5E)-1-(2-(hydroxymethyl)-3-methoxyphenyl) hepta-1,5-diene-3,4-diol, was also achieved by utilizing the unreacted allylic alcohol obtained during the Sharpless kinetic resolution step. Other key steps include the Horner-Wadsworth-Emmons reaction and the diastereoselective reduction of α,β-unsaturated ketone to its corresponding alcohol.

Synthesis and antitumour activity of varitriol and its analogues

Novel analogues of (+)-varitriol have been synthesised via Julia-Kocienski olefination from γ-Dribonolactone. Newly prepared compounds were screened for their in vitro cytotoxicity towards certain human tumours and NCI 60 cancer cell line panel. ARKAT-USA, Inc.

Total synthesis of (+)-varitriol and (+)-6′-epi-varitriol

Total synthesis of (+)-varitriol and its C6′-epimer have been achieved starting from commercially available d-(-)-ribose and o-anisic acid. The key steps involved are Corey Chaykovsky reaction, triethylamine mediated epimerization, and an olefin cross-met

Combined coinage metal catalysis in natural product synthesis: Total synthesis of (+)-varitriol and seven analogs

A modular total synthesis of the natural product (+)-varitriol (1) and seven analogs was achieved by using combined coinage metal catalysis. Starting from enynol 13, reagent-controlled introduction of stereogenic centers and efficient center-to-axis-to-ce

Diastereoselective one-pot Wittig olefination-Michael addition and olefin cross metathesis strategy for total synthesis of cytotoxic natural product (+)-varitriol and its higher analogues

A stereoselective route for the total synthesis of anticancer marine natural product (+)-varitriol (1) is detailed herein. The impressive biological activity and interesting structural features of natural (+)-varitriol fuelled us to undertake the synthesi

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

Stereoselective total synthesis of (+)-varitriol

Stereoselective total synthesis of (+)-varitriol, an antitumor natural product, was accomplished by two versatile strategies starting from the commercially available d-(-)-ribose and ethyl (S)-lactate. The key steps involved in the synthesis of the target molecule are epoxidation, cyclization, dihydroxylation and Diels-Alder reaction.

Total synthesis of (+)-varitriol

The total synthesis of natural (+)-varitriol (1) was accomplished by starting from dimethyl L-tartrate. The key features were a substrate selective and diastereoselective PdII-catalysed bicyclisation of unsaturated protected triol 9 followed by regioselective ring-opening of bicyclic skeleton 10. The absolute configuration of the target was confirmed by single-crystal X-ray analysis for the first time.

First total synthesis of (+)-varitriol

(Chemical Equation Presented) A highly stereoselective total synthesis of (+)-varitriol, an antitumor natural product, has been achieved for the first time from commercially available methyl α,D-mannopyranoside and 2,6-dihydroxybenzoic acid.