Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D
Тип публикации: Journal Article
Дата публикации: 2011-08-25
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
21866884
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-lutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.
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Sidera M., Costa A. M., Vilarrasa J. Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D // Organic Letters. 2011. Vol. 13. No. 18. pp. 4934-4937.
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Sidera M., Costa A. M., Vilarrasa J. Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D // Organic Letters. 2011. Vol. 13. No. 18. pp. 4934-4937.
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TY - JOUR
DO - 10.1021/ol2020187
UR - https://doi.org/10.1021/ol2020187
TI - Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D
T2 - Organic Letters
AU - Sidera, Mireia
AU - Costa, Anna M
AU - Vilarrasa, Jaume
PY - 2011
DA - 2011/08/25
PB - American Chemical Society (ACS)
SP - 4934-4937
IS - 18
VL - 13
PMID - 21866884
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2011_Sidera,
author = {Mireia Sidera and Anna M Costa and Jaume Vilarrasa},
title = {Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D},
journal = {Organic Letters},
year = {2011},
volume = {13},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ol2020187},
number = {18},
pages = {4934--4937},
doi = {10.1021/ol2020187}
}
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MLA
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Sidera, Mireia, et al. “Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D.” Organic Letters, vol. 13, no. 18, Aug. 2011, pp. 4934-4937. https://doi.org/10.1021/ol2020187.
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