Francis Dhoro

University of Western Australia

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Marcus A. Tius

University of Hawaii System

Matthew Piggott

University of Western Australia

Brian W. Skelton

University of Western Australia

Wade F. Petersen

University of Sydney

Roger Hunter

University of Cape Town

Thobela Bixa

University of Cape Town

Louisa Tham

University of Western Australia

Glenn P. A. Yap

University of Delaware

Marco R. Buccini

University of Western Australia

Craig M. Williams

University of Queensland

Cooperative Institutions

University of Hawaii System

University of Hawaiʻi at Mānoa

University of Western Australia

University of Cape Town

Cancer Research Center

University of Delaware

Cancer Center of Hawaii

Imperial College London

Crawley Hospital

University of Hawaii Cancer Center

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

Stereoselective Formation of Quaternary Stereogenic Centers via Alkylation of α-Substituted Malonate-Imidazolidinones

The Journal of Organic Chemistry (2014)

Thobela Bixa Roger Hunter Ana Andrijević Wade F. Petersen Hong Su

A new stereoselective alkylation methodology is presented for formation of chiral, nonracemic quaternary centers via a chiral auxiliary protocol involving α-alkylated malonate imidazolidinones. Based on two X-ray structures of quaternized products, the diastereoselectivity observed may be rationalized via a transition-state involving an s-transC-N conformation of the C-N bond of the auxiliary, with the metal cation (K(+)) chelated into the malonate six-membered hole as a Z-enolate. A deprotection protocol involving ethanethiolate exchange of the imide to the corresponding thioester, followed by a standard Fukuyama reduction and a borohydride reduction, furnishes α,α'-quaternized β-hydroxypropionates in high ee overall.

Malonate

Stereocenter

Dimethyl malonate

Borohydride

10.1021/jo502140d

Cite

Citations (9)

CCDC 639752: Experimental Crystal Structure Determination

The Cambridge Structural Database (2007)

Francis Dhoro T.E. Kristensen Vegar Stockmann Glenn P. A. Yap Marcus A. Tius

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccpgq50

Cite

Citations (0)

Toward the Total Synthesis of Alpkinidine: Michael Addition to Isoquinolinetrione CE Ring-System Synthons

ACS Omega (2022)

Marco R. Buccini Francis Dhoro Louisa Tham Brian W. Skelton Craig M. Williams

Strategies toward the total synthesis of the marine pyrroloacridine alkaloid alpkinidine have been explored, focusing on linking quinonoid CE ring-system synthons with the A ring, followed by condensation to form the B and D rings. The key Michael addition of the ester enolate derived from ethyl o-nitrophenylacetate to 2-methylisoquinoline-1,5,8(2H)-trione proceeded with the wrong regiochemistry. This issue was addressed by incorporating the D-ring nitrogen at an earlier stage, affording advanced intermediates possessing the complete carbon skeleton of alpkinidine. However, attempts to close the D and B rings were unsuccessful. The novel isoquinolinetriones reported here, and the general strategy of connecting CE- and A-ring synthons through Michael additions, may be useful in the synthesis of other pyrrolo- and pyridoacridines, in particular the anticancer lead neoamphimedine and analogues.

Synthon

Michael reaction

10.1021/acsomega.2c02117

Cite

Citations (1)

CCDC 2141773: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Marco R. Buccini Louisa Tham Francis Dhoro Brian W. Skelton Craig M. Williams

10.5517/ccdc.csd.cc29wpgc

Cite

Citations (0)

Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion

Francis Dhoro

Tandem

Source

Cite

Citations (0)

Tandem Alkylation—Cyclization Process via an O,C‐Dianion.

ChemInform (2005)

April R. Banaag Gideon O. Berger Francis Dhoro Derrick B. de los Santos Darryl D. Dixon

Abstract For Abstract see ChemInform Abstract in Full Text.

Tandem

10.1002/chin.200531079

Cite

Citations (0)

CCDC 1054383: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Thobela Bixa Roger Hunter Ana Andrijević Wade F. Petersen Hong Su

10.5517/cc14d5c2

Cite

Citations (0)

Toward the Total Synthesis of Alpkinidine: Synthesis of Haloquinone CE Ring System Synthons and Attempted Nucleophilic Bisannulation

ACS Omega (2022)

Marco R. Buccini Louisa Tham Francis Dhoro Brian W. Skelton Craig M. Williams

Model chemistry involving the bisannulation of 2,3-dichloro-1,4-naphthoquinone with the ester enolate derived from ethyl o-nitrophenylacetic acid, which rapid assembled the ABCD ring system of a pentacyclic pyrroloacridine, has been applied to the attempted synthesis of the marine natural product alpkinidine. The reaction of ethyl o-nitrophenylacetic acid with 6,7-dichloro-2-methylisoquinoline-1,5,8(2H)-trione, required to extend the model strategy to alpkinidine, was unfruitful, giving only complex mixtures. Efforts to direct the regiochemistry of the key Michael substitution step using 6-bromo-2-methylisoquinoline-1,5,8(2H)-trione afforded an adduct sharing the complete carbon skeleton of alpkinidine, but this could not be elaborated to the natural product.

Synthon

Natural product

10.1021/acsomega.2c02116

Cite

Citations (3)

Studies on the total synthesis of polycyclic aromatic alkaloids

Francis Dhoro

Polycyclic aromatic hydrocarbon

Source

Cite

Citations (0)

Tandem alkylation–cyclization process via an O,C-dianion