Summer Research Scholar Projects Available in the Banwell Group 2012-2013
In addition to the projects currently listed on the ANU’s SRS Website the following
additional projects will be available:
1.
Studies Directed Towards the Enantioselective Total Synthesis of 11O-Debenzoyltashironine
The structurally complex natural product 11-O-debenzoyltashironine (1) is a neurotrophic
agent that is considered a lead compound for the treatment of cognitive disorders including
Alzheimer’s disease.1 We have recently synthesized, in enantiopure form, the carbocyclic
framework of this complex natural product using the enzymatically-derived cis-1,2dihydrocatechol (2). Accordingly, this project will seek to exploit these results in moving
towards the completion of a total synthesis of compound 1. The student involved in this
project will gain a variety of experiences in chemical synthesis, including palladiumcatalysed cross-coupling reactions, intramolecular Diels-Alder cycloaddition chemistry
and radical cyclisation protocols.
OH
O
OH
O
HO
OH
OH
I
2
1
References
1. S. P. Cook et al., J. Am. Chem. Soc., 2006, 128, 16440.
2. M. K. Sharma, M. G. Banwell, A. C. Willis and A. D. Rae, Chem. Asian J., 2012,
7, 676.
2.
gem-Dichlorocyclopropanes as Precursors to Novel Analogues of the Potent
New Antibiotic Platencin
The terpenoid platencin (1) has recently been discovered by the Merck Company in the
USA and is regarded as one of the most important new leads for the development
antibiotics that has been discovered in the last twenty years.1 This project will seek to
exploit in-house chemistries, involving highly strained but readily accessible
gemdichlorocyclopropanes, in the rapid assembly of analogues of platencin that would
then be subject to biological evaluation by colleagues in the pharmaceutical industry.
HO2C
OH
O
HO
HN
O
1
References
1. J. Wang et al., Proc. Natl. Acad. Sci. USA, 2007, 104, 7612.
2. K. A. B. Austin, M. G. Banwell and A. C. Willis, Org. Lett., 2008, 10, 4465.
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3.
Chemical Elaboration of Microbially-derived cis-1,2-Dihydrocatechols
to Create New Chirons for Use in the Total Synthesis of Natural Products
cis-Dihydrocatechols of the general form 1 are obtained in large quantity and
enantiomerically pure form through the whole-cell mediated dihydroxylation of the
corresponding arene. We have used such compounds extensively as starting materials in
the chemical synthesis of a range of structurally diverse natural products.1 This project
will involve studies on the chemical manipulation of compound 1 (X=Me) so as to
introduce additional substituents on the diene moiety and thus generate “starting materials”
that should be particularly useful in synthesizing sesquiterpenoid natural products such as
the anti-germination agent tsugicoline A (2).
OH
OH
OH
H
HO
H
O
X
OH
1
2
References
1. See, for example, O. J. Kokas et al., Tetrahedron, 2008, 64, 6444.
4.
Pd[0]-Catalyzed Intramolecular Alder Ene Reactions Leading to
Perhydobenzofurans
We have recently used the title reaction to prepare the crinine alkaloids haemultine (1) and
hamayne (2).1-3 The present project will seek to extend this process to the formation of
oxygen-containing heterocycles such as 3 as part of the development of a concise approach
to the synthesis of the alkaloid galanthamine (4), a compound used clinically for the
symptomatic treatment of Alzheimer’s disease.
HO
OH
H
N
OH
H
O
N
O
O
O
2
1
HO
HO
H
N
O
N
O
MeO
4
3
References
1. A. L. Lehmann, A. C. Willis and M. G. Banwell, Aust. J. Chem., 2010, 63, 1665.
2. L. Petit, M. G. Banwell and A. C. Willis, Org. Lett., 2011, 13, 5800.
3. N. Gao, X. Ma, L. Petit, B. D. Schwartz, M. G. Banwell, A. C. Willis, I. A. Cade
and A. D. Rae, submitted for publication.
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Contact Details for Professor Banwell:
Email (preferred): [email protected]
Phone: 61-2-6125-8202
FAX: 61-2-6125-8114
Mail: Professor Martin Banwell, Research School of Chemistry, The Australian
National University, Canberra, ACT 0200, Australia
Website: http://rsc.anu.edu.au/research/banwell.php