Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin
Publication type: Journal Article
Publication date: 2003-07-10
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12895061
Organic Chemistry
Abstract
The absolute structures of some naturally occurring chiral 2-isopropenyl-2,3-dihydrobenzofurans, (+)-remirol (1a), (+)-remiridiol (1b), (+)-angenomalin (2), and (+)-isoangenomalin (3), were studied by respective chiral synthesis. Kinetic resolutions of racemic 2-isopropenyl-2,3-dihydrobenzofurans, 2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran (4), 4-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran-5-carbaldehyde (8), and 2-isopropenyl-6-(MOM)oxy-2,3-dihydrobenzofuran-5-carbaldehyde (11c), by Sharpless dihydroxylation using (DHQ)(2)AQN or (DHQD)(2)AQN gave the corresponding chiral 2-isopropenyl-2,3-dihydrobenzofurans. Chiral (S)-(+)-4 (99% ee, using (DHQD)(2)AQN) was converted to natural remirol (S)-(+)-1a and then to natural remiridiol (S)-(+)-1b. (S)-(+)-8 (97% ee, using (DHQD)(2)AQN) was converted to natural angenomalin (S)-(+)-2. (R)-(-)-11c (>99% ee, using (DHQ)(2)AQN), was converted to natural isoangenomalin (R)-(+)-3. Thus, the absolute structures of natural remirol (+)-1a and remiridiol (+)-1b and angenomalin (+)-2 were determined to be S, and the structure of natural isoangenomalin (+)-3 was R.
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Yamaguchi S. et al. Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin // Journal of Organic Chemistry. 2003. Vol. 68. No. 16. pp. 6274-6278.
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Yamaguchi S., Muro S., KOBAYASHI M., Miyazawa M., HIRAI Y. Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin // Journal of Organic Chemistry. 2003. Vol. 68. No. 16. pp. 6274-6278.
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TY - JOUR
DO - 10.1021/jo034396j
UR - https://doi.org/10.1021/jo034396j
TI - Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin
T2 - Journal of Organic Chemistry
AU - Yamaguchi, Seiji
AU - Muro, Shizuko
AU - KOBAYASHI, Masahide
AU - Miyazawa, Masahiro
AU - HIRAI, YOSHIRO
PY - 2003
DA - 2003/07/10
PB - American Chemical Society (ACS)
SP - 6274-6278
IS - 16
VL - 68
PMID - 12895061
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2003_Yamaguchi,
author = {Seiji Yamaguchi and Shizuko Muro and Masahide KOBAYASHI and Masahiro Miyazawa and YOSHIRO HIRAI},
title = {Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jo034396j},
number = {16},
pages = {6274--6278},
doi = {10.1021/jo034396j}
}
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Yamaguchi, Seiji, et al. “Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin.” Journal of Organic Chemistry, vol. 68, no. 16, Jul. 2003, pp. 6274-6278. https://doi.org/10.1021/jo034396j.