An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline
Тип публикации: Journal Article
Дата публикации: 2005-08-23
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
16146409
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
[reaction: see text] An application of the phosphine-catalyzed [4 + 2] annulation in the formal synthesis of alstonerine and macroline is reported. A phosphine-catalyzed [4 + 2] reaction between imine 7a and allene 8 formed the D ring of the target indole alkaloids. A subsequent intramolecular Friedel-Crafts acylation provided the C ring of the bridged tetracycle. Deprotection, followed by methylation of the bridged nitrogen, deoxygenation of the C6 ketone, and reduction of the C16 carbethoxy group provided the previously known intermediate 3.
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Tran Y. S., Kwon O. An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline // Organic Letters. 2005. Vol. 7. No. 19. pp. 4289-4291.
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Tran Y. S., Kwon O. An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline // Organic Letters. 2005. Vol. 7. No. 19. pp. 4289-4291.
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TY - JOUR
DO - 10.1021/ol051799s
UR - https://doi.org/10.1021/ol051799s
TI - An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline
T2 - Organic Letters
AU - Tran, Yang S
AU - Kwon, Ohyun
PY - 2005
DA - 2005/08/23
PB - American Chemical Society (ACS)
SP - 4289-4291
IS - 19
VL - 7
PMID - 16146409
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2005_Tran,
author = {Yang S Tran and Ohyun Kwon},
title = {An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline},
journal = {Organic Letters},
year = {2005},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ol051799s},
number = {19},
pages = {4289--4291},
doi = {10.1021/ol051799s}
}
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MLA
Скопировать
Tran, Yang S., and Ohyun Kwon. “An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline.” Organic Letters, vol. 7, no. 19, Aug. 2005, pp. 4289-4291. https://doi.org/10.1021/ol051799s.
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