Enantiodivergent synthesis of cytotoxic styryl lactones from d-xylose. The first total synthesis of (+)- and (−)-crassalactone C

Popsavin, Velimir; Benedeković, Goran; Srećo, Bojana; Francuz, Jovana; Popsavin, Mirjana; Kojić, Vesna; Bogdanović, Gordana; Divjaković, Vladimir

doi:10.1016/j.tet.2009.10.079

Cited by 33 publications

(15 citation statements)

References 39 publications

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“…Diol 181 was prepared by removing of the benzyl protective group from compound in 70% yield. Compound 181 was then reacted with cinnamic acid in the presence of the standard Mitsunobu reagents under the conventional conditions to afford the corresponding coupled compound 182 . According to this strategy, the oxetane 183 was utilized for the synthesis of analogue 178 (5,7‐anhydro‐goniofufurone).…”

Section: Applications Of Mitsunobu Reaction In Total Synthesis Of Natmentioning

confidence: 99%

“…Compound 181 was then reacted with cinnamic acid in the presence of the standard Mitsunobu reagents under the conventional conditions to afford the corresponding coupled compound 182. [239] According to this strategy, the oxetane 183 was utilized for the synthesis of analogue 178 (5,7-anhydro-goniofufurone). Furthermore, in order to enhance the yield of compound 183 (77% yield), the reaction of compound 181 was performed in the absence of cinnamic acid (Ph 3 P, DEAD, at toluene refluxing temperature, 1.5 h).…”

Section: Scheme 18mentioning

confidence: 99%

“…[271] In this strategy, the key reactions are Noyori's asymmetric transfer hydrogenation, Achmatowicz rearrangement, Ferrier-type alkynylation, hydrosilylation-protodesilylation, CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction and Yamaguchi macrolactonization as well as Mitsunobu macrolactonization. The total synthesis of 238 started with providing the intermediate 241 as an appropriate precursor for Mitsunobu reaction from commercially available ethyl acetate (239). Treatment the lithium enolate of 239 with 2-furoyl chloride in THF at -78°C in 2 hr furnished β-keto ester 240 in 78% yield.…”

Section: Scheme 18mentioning

confidence: 99%

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Applications of Mitsunobu Reaction in total synthesis of natural products

Heravi

Ghalavand

Ghanbarian

et al. 2018

Applied Organom Chemis

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The Mitsunobu Reaction allows the conversion of primary and secondary alcohols to esters, phenyl ethers, thioethers and some other compounds. The nucleophile employed should be acidic, since one of the reagents, diethylazodicarboxylate (DEAD) must be protonated during the course of the reaction, preventing from the formation of unwanted side products. In this review, we try to focus on the scope and preparative synthetic applications of Mitsunobu reaction as a key step in the total synthesis of biologically active natural products.

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Section: Applications Of Mitsunobu Reaction In Total Synthesis Of Natmentioning

confidence: 99%

Section: Scheme 18mentioning

confidence: 99%

Section: Scheme 18mentioning

confidence: 99%

See 1 more Smart Citation

Applications of Mitsunobu Reaction in total synthesis of natural products

Heravi

Ghalavand

Ghanbarian

et al. 2018

Applied Organom Chemis

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show abstract

“…For example, a group of 3,5‐anhyrdo nucleosides containing thymine, cytosine, adenine, and guanine nucleobases were synthesized as conformationally constrained analogs of 2′,5′‐linked oligoribonucleotides to study the conformational effects on their bioactivities . In 2009, the total synthesis of naturally occurring antitumor agents (+)‐goniofufurone, 7‐ epi ‐(+)‐goniofufurone, and (+)‐crassalactone C was reported by Popsavin and co‐workers . In the meantime, they also synthesized the unnatural enantiomers and two conformationally constrained analogs ( 218 ) and ent‐ 218 bearing 3,5‐anhydro moieties of these natural products (Figure ).…”

Section: 5‐anhydro Furanose (26‐dioxabicyclo[320]heptane) and 4mentioning

confidence: 99%

The Construction of Anhydro Monosaccharides

Xie

Lin

et al. 2016

Asian J Org Chem

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Anhydro monosaccharide is as pecific and distinctive category of carbohydrates, which is found in many naturally deriveda nd artificial bioactive substrates. In the field of organic chemistry,s ome anhydro sugars can be used as common synthons to construct different carbohydrate structures. The development of efficient methodologies for the constructiono fv ariousa nhydro sugar fragments is very important in carbohydrate chemistry,w hich has attracted considerable attention in the past few years. This reviewm ainly covers the development of new synthetic methods since 2000 and gives an overview of the development in the formation of anhydro monosaccharide structures. It systematically summarizes all methodst oe stablish an intramolecular ether bridge in furanose and pyranose structures, which are the mostc ommonly used monosaccharide fragments in carbohydrate chemistry.

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“…Meldrum's acid can readily undergo enolate formation with Et 3 N for further condensation reaction. Popsavin, reported that furofuranone moiety 83 was prepared from Meldrum's acid and sugar lactol 82 using Et 3 N in a moderate yield in the total synthesis of goniofufurone (Scheme ).…”

Section: Sequential Formation Of Furofuranonesmentioning

confidence: 99%

Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Peng

Ylagan

Siu

et al. 2015

Chemistry An Asian Journal

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The synthesis and application of [3.3.0]furofuranone species has received considerable attention from the scientific community. During the last twenty years, there has been a remarkable increase in publications focusing on their relevant method development as well as applications to natural product synthesis. This tutorial review discusses instructive examples to give a special emphasis on the development of new synthetic approaches and important applications to the total synthesis of natural products.

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Enantiodivergent synthesis of cytotoxic styryl lactones from d-xylose. The first total synthesis of (+)- and (−)-crassalactone C

Cited by 33 publications

References 39 publications

Applications of Mitsunobu Reaction in total synthesis of natural products

Applications of Mitsunobu Reaction in total synthesis of natural products

The Construction of Anhydro Monosaccharides

Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

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