Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration
Publication type: Journal Article
Publication date: 2011-06-03
scimago Q3
wos Q3
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
21628913
General Chemistry
Drug Discovery
General Medicine
Abstract
Synthesis of dehydoriso-β-lapachone (1) in both racemic and enantioenriched forms is achieved starting from reduced naphthoquinone equivalents. As for the synthesis of enantioenriched dehydroiso-β-lapachone, introduction of the asymmetric center was carried out by catalytic asymmetric epoxidation of the unfunctionalized trisubstituted olefin using Shi epoxidation diketal catalyst. The construction of isopropenylfurano-1,2-(β)-naphthoquinone was carried out by acidic ring-opening reaction of the epoxynaphthalene and the following diammonium cerium(IV) nitrate (CAN) oxidation. The absolute configuration of naturally occurring (-)-dehydroiso-β-lapachone was finally determined as (R) by comparing the measured optical rotation value of the synthetic (R)-dehydroiso-β-lapachone.
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11
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Kimachi T. et al. Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration // Chemical and Pharmaceutical Bulletin. 2011. Vol. 59. No. 6. pp. 753-756.
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Kimachi T., Torii E., Kobayashi Y., Doe M., Ju-ichi M. Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration // Chemical and Pharmaceutical Bulletin. 2011. Vol. 59. No. 6. pp. 753-756.
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TY - JOUR
DO - 10.1248/cpb.59.753
UR - https://doi.org/10.1248/cpb.59.753
TI - Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration
T2 - Chemical and Pharmaceutical Bulletin
AU - Kimachi, Tetsutaro
AU - Torii, Eri
AU - Kobayashi, Yusuke
AU - Doe, Misae
AU - Ju-ichi, Motoharu
PY - 2011
DA - 2011/06/03
PB - Pharmaceutical Society of Japan
SP - 753-756
IS - 6
VL - 59
PMID - 21628913
SN - 0009-2363
SN - 1347-5223
ER -
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BibTex (up to 50 authors)
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@article{2011_Kimachi,
author = {Tetsutaro Kimachi and Eri Torii and Yusuke Kobayashi and Misae Doe and Motoharu Ju-ichi},
title = {Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {59},
publisher = {Pharmaceutical Society of Japan},
month = {jun},
url = {https://doi.org/10.1248/cpb.59.753},
number = {6},
pages = {753--756},
doi = {10.1248/cpb.59.753}
}
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MLA
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Kimachi, Tetsutaro, et al. “Synthesis of Biologically Active (-)-Dehydroiso-.BETA.-lapachone and the Determination of Its Absolute Configuration.” Chemical and Pharmaceutical Bulletin, vol. 59, no. 6, Jun. 2011, pp. 753-756. https://doi.org/10.1248/cpb.59.753.