Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H

Vulović, Bojan; Kolarski, Dusan; Bihelović, Filip; Matović, Radomir; Gruden, Maja; Saičić, Radomir N.

doi:10.1021/acs.orglett.6b01898

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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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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.

Source:
Organic Letters, 2016, 18, 15, 3886-3889

Publisher:

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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	15
	11

TY  - 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 . .