Total synthesis of 6-epiprelactone-V via a syn-selective oxygen tethered intramolecular Michael reaction

Chandrasekhar, S.; Rambabu, Ch.; Prakash, S. Jaya

doi:10.1016/j.tetlet.2005.12.012

Cited by 13 publications

(2 citation statements)

References 30 publications

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“…In the year 2006, Chandrasekhar et al . reported the synthesis of epi ‐prelactone V 1 f , a non‐natural enantiomer of prelactone by a syn ‐selective oxygen tethered intramolecular Michael reaction [30] . Initially ( S )‐malic acid 87 was converted into dimethyl malate 88 using methanol in BF 3 ⋅ OEt 2 .…”

Section: Synthetic Approaches Of Prelactonesmentioning

confidence: 99%

“…In the year 2006, Chandrasekhar et al reported the synthesis of epi-prelactone V 1 f, a non-natural enantiomer of prelactone by a syn-selective oxygen tethered intramolecular Michael reaction. [30] Initially (S)-malic acid 87 was converted into dimethyl malate 88 using methanol in BF 3 • OEt 2 . Next, the diester 88 was subjected for α-alkylation with methyl iodide using LHMDS in THF at À 78 °C to get methyl substituted dimethyl malate 89 in good yield with high diastereoselectivity (12 : 1), but the diastereomers could not be separated by chromatography.…”

Section: Chandrasekhar's Approach For Epi-prelactone Vmentioning

confidence: 99%

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Synthetic Approaches of Prelactone and Its Analogues: A Review

et al. 2021

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In this review we have discussed the synthetic approaches of prelactones and their epimers from 1997 to date. The presence of unique molecular architecture and its high biological importance enhanced the research activity over the last two decades. Most of the syntheses involve either a chiral auxiliary, chiral pool or catalytic enantioselective approaches as a key step. Overall this review highlights the contribution from different research groups in the total synthesis of various prelactones.

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Section: Synthetic Approaches Of Prelactonesmentioning

confidence: 99%

Section: Chandrasekhar's Approach For Epi-prelactone Vmentioning

confidence: 99%

Synthetic Approaches of Prelactone and Its Analogues: A Review

et al. 2021

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Asymmetric Sequential Aza‐Diels‐Alder and O‐Michael Addition: Efficient Construction of Chiral Hydropyrano[2,3‐b]pyridines

et al. 2012

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Recent advances in the applications of Wittig reaction in the total synthesis of natural products containing lactone, pyrone, and lactam as a scaffold

et al. 2019

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The Wittig reaction enables the synthesis of an alkene from the reaction of an aldehyde or ketone with the ylide generated from a phosphonium salt. Undoubtedly, its usefulness in the synthesis of alkenes in an anticipated manner has resulted in the introduction of an attractive principle in synthetic organic chemistry, particularly in the total synthesis of natural products. In this review, we try to highlight the applications of Wittig reaction in total synthesis of natural products. Worthy to mention that due to the vast numbers of related achievements, described in chemical literature, we had to limit ourselves to the applications of Wittig reaction to the total synthesis of natural products that contain lactone, pyrone, or lactam as scaffold in their complex structures.

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Total synthesis of 6-epiprelactone-V via a syn-selective oxygen tethered intramolecular Michael reaction

Cited by 13 publications

References 30 publications

Synthetic Approaches of Prelactone and Its Analogues: A Review

Synthetic Approaches of Prelactone and Its Analogues: A Review

Asymmetric Sequential Aza‐Diels‐Alder and O‐Michael Addition: Efficient Construction of Chiral Hydropyrano[2,3‐b]pyridines

Recent advances in the applications of Wittig reaction in the total synthesis of natural products containing lactone, pyrone, and lactam as a scaffold

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