Total Synthesis of Entecavir

Velasco, Javier; Ariza, Xavier; Badía, Laura; Bartra, M.; Berenguer, Ramon; Farràs, Jaume; Gallardo, Joan; García, Jordi; Gasanz, Yolanda

doi:10.1021/jo400607v

Cited by 38 publications

(18 citation statements)

References 26 publications

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“…Because of its lack of significant adverse effects and the low risk of inducing long‐term resistance has been used for the treatment of chronic patients such as hepatitis B . A straightforward synthesis of 222 was accomplished in 11 steps from commercially available starting materials 4‐trimethylsilyl‐3‐butyn‐2‐one ( 223 ) and acrolein through stereoselective boron−aldol reaction, Cp 2 TiCl‐catalyzed intramolecular radical addition and Mitsunobu reaction as key steps by Farràs and co‐workers in 2013 . Total synthesis of ( 222 ) began with preparation of pure syn diol 224 via the enantioselective aldol reaction between ( 223 ) and acrolein performed with (+)‐chlorodiisopinocampheylborane as a source of chirality followed by the in situ reduction of the resulting chelate with LiBH 4 and oxidative work up with H 2 O 2 and NaOAc with 37% overall yield.…”

Section: Applications Of Mitsunobu Reaction In Total Synthesis Of Natmentioning

confidence: 99%

“…[261] A straightforward synthesis of 222 was accomplished in 11 steps from commercially available starting materials 4-trimethylsilyl-3-butyn-2-one (223) and acrolein through stereoselective boron−aldol reaction, Cp 2 TiCl-catalyzed intramolecular radical addition and Mitsunobu reaction as key steps by Farràs and co-workers in 2013. [262] Total synthesis of (222) began with preparation of pure syn diol 224 via the enantioselective SCHEME 45 The total synthesis of molecule 218 aldol reaction between (223) and acrolein performed with (+)-chlorodiisopinocampheylborane as a source of chirality followed by the in situ reduction of the resulting chelate with LiBH 4 and oxidative work up with H 2 O 2 and NaOAc with 37% overall yield. After 7 steps, fragment 224 transformed into 225 as an appropriate precursor for Mitsunobu coupling reaction.…”

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%

Applications of Mitsunobu Reaction in total synthesis of natural products

Heravi

Ghalavand

Ghanbarian

et al. 2018

Applied Organom Chemis

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“…Finally, the same year, Gasanz et al also outlined a concised methodology from acyclic precursors with a newly developed synthetic tool toward the total synthesis of entecavir ( Figure 14) [29]. Indeed, they refined some key components for the preparation of 3 such as a stereoselective aldol reaction with acrolein and a Ti(III)-mediated radical intramolecular cyclization.…”

Section: Precursor Of the Final Sugar Moiety A Further Epoxidation Imentioning

confidence: 99%

Recent Progress for the Synthesis of Selected Carbocyclic Nucleosides

et al. 2015

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Nucleoside analogs are extremely useful for the development of therapeutic agents to control viral diseases and cancer. Among the numerous modifications on the nucleoside skeleton, replacement of the oxygen of the furanose ring by a CH2 group resulted in increased flexibility and higher resistance to phosphorylases and led to carbocyclic nucleoside analogs (or carbanucleosides). The broad spectrum of biological activities of carbocyclic nucleosides led to tremendous research interest in their syntheses. The article documents recent strategies for the synthesis of active carbocyclic nucleosides by presenting individual case studies, such as the neplanocins, entecavir and selected fluorinated carbocyclic nucleosides. Furthermore, it provides new insights into new directions for more potent and active carbocyclic nucleoside analogs.

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“…The introduction of IrCl(CO)(PPh 3 ) 2 /H 2 in the reaction conditions allowed the reduction of the final radical (Scheme 71). 108 temperature of stereodefined terpenic skeletons without enzymatic assistance is remarkable. In this context, the main limitation of this bioinspired approach is, in fact, its extraordinary stereoselectivity, which avoids obtaining cis-fused decalins and/or substituents in axial positions.…”

Section: Miscellaneousmentioning

confidence: 99%