Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H
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2016
Authors
Vulović, Bojan
Kolarski, Dusan
Bihelović, Filip

Matović, Radomir

Gruden, Maja

Saičić, Radomir N.

Article (Published version)

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Show full item recordAbstract
1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.
Source:
Organic Letters, 2016, 18, 15, 3886-3889Publisher:
- American Chemical Society (ACS)
Funding / projects:
- The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
- Serbian Academy of Sciences and Arts [F193]
DOI: 10.1021/acs.orglett.6b01898
ISSN: 1523-7060
PubMed: 27456978
WoS: 000381236300095
Scopus: 2-s2.0-84981188263
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IHTMTY - JOUR AU - Vulović, Bojan AU - Kolarski, Dusan AU - Bihelović, Filip AU - Matović, Radomir AU - Gruden, Maja AU - Saičić, Radomir N. PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1847 AB - 1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer. PB - American Chemical Society (ACS) T2 - Organic Letters T1 - Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H VL - 18 IS - 15 SP - 3886 EP - 3889 DO - 10.1021/acs.orglett.6b01898 ER -
@article{ author = "Vulović, Bojan and Kolarski, Dusan and Bihelović, Filip and Matović, Radomir and Gruden, Maja and Saičić, Radomir N.", year = "2016", abstract = "1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.", publisher = "American Chemical Society (ACS)", journal = "Organic Letters", title = "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H", volume = "18", number = "15", pages = "3886-3889", doi = "10.1021/acs.orglett.6b01898" }
Vulović, B., Kolarski, D., Bihelović, F., Matović, R., Gruden, M.,& Saičić, R. N.. (2016). Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters American Chemical Society (ACS)., 18(15), 3886-3889. https://doi.org/10.1021/acs.orglett.6b01898
Vulović B, Kolarski D, Bihelović F, Matović R, Gruden M, Saičić RN. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters. 2016;18(15):3886-3889. doi:10.1021/acs.orglett.6b01898 .
Vulović, Bojan, Kolarski, Dusan, Bihelović, Filip, Matović, Radomir, Gruden, Maja, Saičić, Radomir N., "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H" in Organic Letters, 18, no. 15 (2016):3886-3889, https://doi.org/10.1021/acs.orglett.6b01898 . .