Elsevier
Tetrahedron
,  том 38 ,  издание 20 ,  страницы 3079-3084

Approaches to the regiospecific synthesis of Anthracycline antibiotics

Тип публикации: Journal Article
Дата публикации: 1982-01-01
Elsevier
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Synthetic approaches to anthracycline antibiotics were studied through the use of Claisen rearrangements on 1-methallyloxy-5-methoxyantraquinone (9) which required reducing conditions to proceed through a hydroquinone intermediate in situ. 1-(2′-Methylene-4′-pentenoxy)-5-methoxyanthraquinone (13) underwent a similar reductive rearrangement but also produced a spiro compound 16 as a result of an ene reaction between the phenol and side chain double bond. 1-Hydroxy-2-methally-5-methoxyanthraquinone (11) could not be oxidized to quinizarin 17. 1-Hydroxy-2-methally-5,9,10-trimethoxyanthracene (21) was oxidatively coupled to the dimer at C-2. Dimer 23 reacted with diazomethane to form a 1,3-dipolar adduct 24.
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BALDWIN J. E., Rajeckas A. J. Approaches to the regiospecific synthesis of Anthracycline antibiotics // Tetrahedron. 1982. Vol. 38. No. 20. pp. 3079-3084.
ГОСТ со всеми авторами (до 50) Скопировать
BALDWIN J. E., Rajeckas A. J. Approaches to the regiospecific synthesis of Anthracycline antibiotics // Tetrahedron. 1982. Vol. 38. No. 20. pp. 3079-3084.
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TY - JOUR
DO - 10.1016/0040-4020(82)80196-8
UR - https://doi.org/10.1016/0040-4020(82)80196-8
TI - Approaches to the regiospecific synthesis of Anthracycline antibiotics
T2 - Tetrahedron
AU - BALDWIN, JACK E.
AU - Rajeckas, Algis J
PY - 1982
DA - 1982/01/01
PB - Elsevier
SP - 3079-3084
IS - 20
VL - 38
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1982_BALDWIN,
author = {JACK E. BALDWIN and Algis J Rajeckas},
title = {Approaches to the regiospecific synthesis of Anthracycline antibiotics},
journal = {Tetrahedron},
year = {1982},
volume = {38},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/0040-4020(82)80196-8},
number = {20},
pages = {3079--3084},
doi = {10.1016/0040-4020(82)80196-8}
}
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BALDWIN, JACK E., and Algis J Rajeckas. “Approaches to the regiospecific synthesis of Anthracycline antibiotics.” Tetrahedron, vol. 38, no. 20, Jan. 1982, pp. 3079-3084. https://doi.org/10.1016/0040-4020(82)80196-8.