Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations
Publication type: Journal Article
Publication date: 2016-06-15
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27266504
Organic Chemistry
Abstract
The fused 6/7/5/6/6-membered (ABCDE) ring system of talatisamine was synthesized in 22 steps. After preparation of the AE-ring structure from 2-(ethoxycarbonyl)cyclohexanone, elaboration of the carboskeleton was realized by sequential additions of allyl magnesium bromide and the lithiated C-ring. The C11-bridgehead radical derived from the ACE-ring underwent the 7-endo cyclization with the enone moiety to form the B-ring in C10-stereoselective and C11-stereospecific manners. The 6-endo cyclization of the remaining D-ring was in turn attained by using the silyl enol ether as the nucleophile and the PhSeCl-activated olefin as the electrophile. These radical and cationic cyclizations were demonstrated to be highly chemoselective, and they significantly contributed to streamlining the route to the intricately fused pentacycle of talatisamine.
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Total citations:
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Citations from 2024:
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(11.12%)
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Tabuchi T., Urabe D., Inoue M. Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations // Journal of Organic Chemistry. 2016. Vol. 81. No. 21. pp. 10204-10213.
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Tabuchi T., Urabe D., Inoue M. Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations // Journal of Organic Chemistry. 2016. Vol. 81. No. 21. pp. 10204-10213.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.6b01011
UR - https://doi.org/10.1021/acs.joc.6b01011
TI - Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations
T2 - Journal of Organic Chemistry
AU - Tabuchi, Toshiki
AU - Urabe, Daisuke
AU - Inoue, Masayuki
PY - 2016
DA - 2016/06/15
PB - American Chemical Society (ACS)
SP - 10204-10213
IS - 21
VL - 81
PMID - 27266504
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2016_Tabuchi,
author = {Toshiki Tabuchi and Daisuke Urabe and Masayuki Inoue},
title = {Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.6b01011},
number = {21},
pages = {10204--10213},
doi = {10.1021/acs.joc.6b01011}
}
Cite this
MLA
Copy
Tabuchi, Toshiki, et al. “Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations.” Journal of Organic Chemistry, vol. 81, no. 21, Jun. 2016, pp. 10204-10213. https://doi.org/10.1021/acs.joc.6b01011.