Papers by Sibadatta Senapati
Journal of Organic Chemistry, Sep 14, 2018
The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal... more The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal cis-enyne unit. In this work, we document the first total synthesis of notoryne, confirming its assigned relative and absolute configurations. The devised route comprises a glucose diacetonide-derived chiral pool intermediate as the starting point and 5- endo bromo-etherification for making the key bis-furan unit, anomeric C-allylation, as well as a relay cross-metathesis to install the cis-enyne unit.
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ACS omega, Sep 24, 2020
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Organic and Biomolecular Chemistry, 2021
A diastereoselective gold cyclisation and a Sharpless asymmetric dihydroxylation–cycloetherificat... more A diastereoselective gold cyclisation and a Sharpless asymmetric dihydroxylation–cycloetherification protocol were carried out for the construction of the key disaccharide unit (C14–C28) of eribulin mesylate with a linear sequence of 14 steps.
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Journal of Chemical Sciences, Jul 17, 2021
In this manuscript we document the details of the synthesis of four diastereomers of notoryne. Th... more In this manuscript we document the details of the synthesis of four diastereomers of notoryne. The synthesis of one of the diastereomer having a similar relative stereochemistry of substituents on the both THF rings like notoryne, however, being the relative stereochemistry between the bridging carbon of these two THF units is changed from anti to syn has been executed mainly to learn how the ring carbon chemical shifts vary with this change. Interestingly, the deviations are found mainly for the carbons of THF ring that bears the Br-group. In addition to this isomer, three more diastereomers having the relative stereochemistry of substituents on either of the THF rings varied have been also synthesized. All four diastereomers have been subjected for extensive NMR studies and their 13 C NMR chemical shifts have been compared with notoryne and laurendecumenyne B. In addition, chemical shifts for the four diastereomers along with these natural products were calculated with the help of DFT calculations and compared to the experimentally obtained chemical shift values. The notoryne diastereomer 1 having similar relative stereochemistry of substituents on both THF rings and being the relative stereochemistry between the bridging carbon of these two THF units is changed from anti to syn, has been executed to learn how the ring carbon chemical shifts vary with this change. Also, the three other diastereomers 2–4 have been synthesized and a detailed NMR analysis has been carried out/compared.
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Journal of Chemical Sciences, 2021
In this manuscript we document the details of the synthesis of four diastereomers of notoryne. Th... more In this manuscript we document the details of the synthesis of four diastereomers of notoryne. The synthesis of one of the diastereomer having a similar relative stereochemistry of substituents on the both THF rings like notoryne, however, being the relative stereochemistry between the bridging carbon of these two THF units is changed from anti to syn has been executed mainly to learn how the ring carbon chemical shifts vary with this change. Interestingly, the deviations are found mainly for the carbons of THF ring that bears the Br-group. In addition to this isomer, three more diastereomers having the relative stereochemistry of substituents on either of the THF rings varied have been also synthesized. All four diastereomers have been subjected for extensive NMR studies and their 13 C NMR chemical shifts have been compared with notoryne and laurendecumenyne B. In addition, chemical shifts for the four diastereomers along with these natural products were calculated with the help of DFT calculations and compared to the experimentally obtained chemical shift values. The notoryne diastereomer 1 having similar relative stereochemistry of substituents on both THF rings and being the relative stereochemistry between the bridging carbon of these two THF units is changed from anti to syn, has been executed to learn how the ring carbon chemical shifts vary with this change. Also, the three other diastereomers 2–4 have been synthesized and a detailed NMR analysis has been carried out/compared.
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Synthesis, 2021
A highly diastereoselective total synthesis of several bis-THF C15 acetogenin natural products, c... more A highly diastereoselective total synthesis of several bis-THF C15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenynes A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, SN2 halogenation, and a relay cross metathesis.
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The Journal of Organic Chemistry, 2018
The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal... more The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal cis-enyne unit. In this work, we document the first total synthesis of notoryne, confirming its assigned relative and absolute configurations. The devised route comprises a glucose diacetonide-derived chiral pool intermediate as the starting point and 5- endo bromo-etherification for making the key bis-furan unit, anomeric C-allylation, as well as a relay cross-metathesis to install the cis-enyne unit.
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Organic & Biomolecular Chemistry, 2021
A diastereoselective gold cyclisation and a Sharpless asymmetric dihydroxylation–cycloetherificat... more A diastereoselective gold cyclisation and a Sharpless asymmetric dihydroxylation–cycloetherification protocol were carried out for the construction of the key disaccharide unit (C14–C28) of eribulin mesylate with a linear sequence of 14 steps.
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Papers by Sibadatta Senapati