Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones
Тип публикации: Journal Article
Дата публикации: 2000-10-01
scimago Q3
wos Q2
white level БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
A Claisen rearrangement based methodology for spiroannulation of a cyclopentane ring to cyclic precursors and its application in the formal total synthesis of acorones 1 is described. Thus, Claisen rearrangement of 2-cycloalkylideneethanols 12 with 2-methoxypropene and a catalytic amount of mercuric acetate generates 4,4-substituted hex-5-en-2-ones 13. Ozonolytic cleavage of the terminal olefin in the enones 13 and intramolecular aldol condensation of the resulting keto-aldehydes 14 furnishes the spiroannulated compounds 15.
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Srikrishna A., Prachethan Kumar P. Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones // Tetrahedron. 2000. Vol. 56. No. 41. pp. 8189-8195.
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Srikrishna A., Prachethan Kumar P. Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones // Tetrahedron. 2000. Vol. 56. No. 41. pp. 8189-8195.
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TY - JOUR
DO - 10.1016/S0040-4020(00)00743-2
UR - https://doi.org/10.1016/S0040-4020(00)00743-2
TI - Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones
T2 - Tetrahedron
AU - Srikrishna, A.
AU - Prachethan Kumar, P.
PY - 2000
DA - 2000/10/01
PB - Elsevier
SP - 8189-8195
IS - 41
VL - 56
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2000_Srikrishna,
author = {A. Srikrishna and P. Prachethan Kumar},
title = {Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones},
journal = {Tetrahedron},
year = {2000},
volume = {56},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/S0040-4020(00)00743-2},
number = {41},
pages = {8189--8195},
doi = {10.1016/S0040-4020(00)00743-2}
}
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MLA
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Srikrishna, A., and P. Prachethan Kumar. “Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of (±)-Acorone and Isoacorones.” Tetrahedron, vol. 56, no. 41, Oct. 2000, pp. 8189-8195. https://doi.org/10.1016/S0040-4020(00)00743-2.
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