A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K
Тип публикации: Journal Article
Дата публикации: 2001-09-27
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
11594807
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
[reaction: see text]. A convenient and asymmetric protocol for the synthesis of chiral oligoisoprenoids is described. Typically, a C14 vitamin E side chain 5 was synthesized in 47% yield over four steps. Isomeric purity of 5 was upgraded to >99% R at C-2 and 97% R at C-6 by the statistical formation of stereoisomeric p-phenylenebisurethanes and their diastereomeric separation. In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.
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Huo S., Negishi E. A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K // Organic Letters. 2001. Vol. 3. No. 21. pp. 3253-3256.
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Huo S., Negishi E. A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K // Organic Letters. 2001. Vol. 3. No. 21. pp. 3253-3256.
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TY - JOUR
DO - 10.1021/ol010142d
UR - https://doi.org/10.1021/ol010142d
TI - A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K
T2 - Organic Letters
AU - Huo, Shouquan
AU - Negishi, Ei-ichi
PY - 2001
DA - 2001/09/27
PB - American Chemical Society (ACS)
SP - 3253-3256
IS - 21
VL - 3
PMID - 11594807
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2001_Huo,
author = {Shouquan Huo and Ei-ichi Negishi},
title = {A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K},
journal = {Organic Letters},
year = {2001},
volume = {3},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/ol010142d},
number = {21},
pages = {3253--3256},
doi = {10.1021/ol010142d}
}
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Huo, Shouquan, and Ei-ichi Negishi. “A Convenient and Asymmetric Protocol for the Synthesis of Natural Products Containing Chiral Alkyl Chains via Zr-Catalyzed Asymmetric Carboalumination of Alkenes. Synthesis of Phytol and Vitamins E and K.” Organic Letters, vol. 3, no. 21, Sep. 2001, pp. 3253-3256. https://doi.org/10.1021/ol010142d.
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