Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G
Тип публикации: Journal Article
Дата публикации: 2020-04-07
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ISSN: 15237060, 15237052
PubMed ID:
32255356
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
Herein we report the stereochemical revision of peribysins A, B, C, F, and G, guided by enantiospecific total synthesis starting from (+)-nootkatone. Furthermore, we reconfirmed the absolute stereochemistry of peribysin Q. The highlights of the synthesis are enone transposition and kinetic iodination resulting in separation of diastereomers. Our findings coupled with synthetic and biological data previously reported by Danishefsky's group suggest that the original stereochemistries of peribysins A, B, C, F, and G were misassigned.
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Athawale P. R. et al. Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G // Organic Letters. 2020. Vol. 22. No. 8. pp. 3104-3109.
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Athawale P. R., P. Kalmode H., Motiwala Z., Kulkarni K. A., Reddy D. S. Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G // Organic Letters. 2020. Vol. 22. No. 8. pp. 3104-3109.
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TY - JOUR
DO - 10.1021/acs.orglett.0c00857
UR - https://doi.org/10.1021/acs.orglett.0c00857
TI - Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G
T2 - Organic Letters
AU - Athawale, Paresh R
AU - P. Kalmode, Hanuman
AU - Motiwala, Zenia
AU - Kulkarni, Kiran A.
AU - Reddy, Dumbala Srinivasa
PY - 2020
DA - 2020/04/07
PB - American Chemical Society (ACS)
SP - 3104-3109
IS - 8
VL - 22
PMID - 32255356
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2020_Athawale,
author = {Paresh R Athawale and Hanuman P. Kalmode and Zenia Motiwala and Kiran A. Kulkarni and Dumbala Srinivasa Reddy},
title = {Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.0c00857},
number = {8},
pages = {3104--3109},
doi = {10.1021/acs.orglett.0c00857}
}
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Athawale, Paresh R., et al. “Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G.” Organic Letters, vol. 22, no. 8, Apr. 2020, pp. 3104-3109. https://doi.org/10.1021/acs.orglett.0c00857.
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