Total synthesis of (+)-decytospolides A and B

Pazó, Marta; Zúñiga, Andrea; Pérez, Manuel; Gómez, Generosa; Fall, Yagamare

doi:10.1016/j.tetlet.2015.04.055

Cited by 9 publications

(4 citation statements)

References 11 publications

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“…The physical and spectral data of the synthetic decytospolide A (1) and B (2) were consistent with those of the reported values (Scheme 4). 2,10 In conclusion, we have improved the stereoselectivity and chemical yield of oxypalladation of 6-(benzyloxy)-7hydroxydodec-2-enyl 2-naphthoates to form the 2,6-cistetrahydropyran ring. This methodology was applied to the stereoselective synthesis of decytospolide A (1) and B (2).…”

Section: Paper Syn Thesismentioning

confidence: 89%

“…Liu and co-workers used the palladium-catalyzed decarboxylative allylation of 3,4-dihydro-2H-pyran to form the THP ring. 5 Quite recently, Prins reaction, 6 regioselective reduction of the carbonyl group, 7 and olefin metathesis, 8 intramolecular oxa-Michael reaction, 9 and 3,3-sigmatropic rearrangement 10 were applied to the synthesis of decytospolides. We have developed a palladium(II)-catalyzed diastereoselective cyclization (oxypalladation and azapalladation) for the construction of THP, 11 piperidine, 12 and pyrrolidine 13 rings.…”

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confidence: 99%

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Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation

2016

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Section: Paper Syn Thesismentioning

confidence: 89%

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confidence: 99%

Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation

2016

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“…111 Later Fall et al synthesized decytospolide by using glycal aldehyde 157 as the chiral building block, which is easily synthesized from glucal. 112 The key step in this synthesis involves stereoselective [3,3]-sigmatropic rearrangement. The overall yield was found to be 16%.…”

Section: Short Review Synthesis 6 Natural Product Synthesismentioning

confidence: 99%

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

Mukherjee,

Kundu,

Das

et al. 2023

Synthesis

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The development of stereoselective synthetic routes for C-glycosides has attracted immense attention from carbohydrate chemists in the last two decades. In this review, progress made in the last decade towards the synthesis of C-glycosides using glycals as a precursor are discussed. Glycals have been extensively manipulated to generate oxocarbenium cation or glycosyl anion to form C-C bond at the anomeric position through attack with C-nucleophiles or transition metal catalyzed coupling reactions. Recent reports on carbon Ferrier, intramolecular Cope, Claisen rearrangements, various coupling reactions in the presence or absence of directing groups are deliberated herein. Contemporary applications of these reactions in the syntheses of natural products, drugs and scaffolds with bioactive potential are briefly discussed.

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“…Gómez and Fall groups reported using a [3,3]-sigmatropic rearrangement for the synthesis of 2,6-cis-tetrahydropyrans imbedded in 1 and 2. 9 A final synthesis was reported using intramolecular oxapalladation for the construction of 2,6-cis-tetrahydropyran by Makabe group. 10 Recently, gem-disubstituent 11 (Thorpe-Ingold) effect promoted tandem allylic oxidation-intramolecular oxa-Michael reactions of diol (A) have been successfully applied to the stereoselective synthesis of 2,6-cis-tetrahydropyrans (C) via conformationally more stable intermediate B1 in excellent stereoselectivity (dr >25:1), reported by Hong and co-workers (Scheme 1).…”

Section: Figure 1 Decytospolides a And Bmentioning

confidence: 99%