Chemistry Reference
In-Depth Information
7.8 Concluding Remarks
In this chapter, applications of amidine, guanidine and phosphazene superbases to the
synthesis of natural products have been discussed. Many structurally complex natural
products have been synthesized efficiently and elegantly by making use of the reactions
described. Currently, much attention is focussed on the development of chiral superbases
and their application to asymmetric reactions. Such catalytic asymmetric reactions are
expected to offer exciting and efficient new approaches to the synthesis of natural products
and biologically active compounds.
References
1. Simoni, D., Invidiata, F.P., Manfredini, S.et al. (1997) Facile synthesis of 2-nitroalkanols by
tetramethylguanidine (TMG)-catalysed addition of primary nitroalkanes to aldehydes and
alicyclic ketones. Tetrahedron Letters, 38, 2749-2752.
2. Ishikawa, T., Shimizu, Y., Kudoh, T. and Saito, S. (2003) Conversion of D -glucose to cyclitol with
hydroxymethyl substituent via intramolecular silyl nitronate cycloaddition reaction: application
to total synthesis of ( þ )-cyclophellitol. Organic Letters, 5, 3879-3882.
3. Luzzio, F.A. and Fitch, R.W. (1999) Formal synthesis of ( þ )- and ( )-perhydrohistrionicotoxin:
a double Henry /enzymatic desymmetrization route to the Kishi lactam. The Journal of Organic
Chemistry, 64, 5485-5493.
4. Aratani, M., Dunkerton, L.U., Fukuyama, T. et al. (1975) Synthetic studies on histrionicotoxins.
I. Stereocontrolled synthesis of ( )-perhydrohistrionicotoxin. The Journal of Organic Chemistry,
40, 2009-2001.
5. Madin, A., O Donnell, C.J., Oh, T. et al. (1999) Total synthesis of ( )-gelsemine. Angewandte
Chemie - International Edition, 38, 2934-2936.
6. Kraus, G.A., Zhang, N., Verkade, J.G. et al. (2000) Deprotonation of benzylic ethers using a
hindered phosphazene base. A synthesis of benzofurans from ortho-substituted benzaldehydes.
Organic Letters, 2, 2409-2410.
7. Novikov, A.V., Kennedy, A.R. and Rainier, J.D. (2003) Sulfur ylide-initiated thio-Claisen
rearrangements. The synthesis of highly substituted indolines. The Journal of Organic Chemistry,
68, 993-996.
8. Henderson, D.A., Collier, P.N., Pav ´ ,G.et al. (2006) Studies on the total synthesis of
lactonamycin: construction of model ABCD ring systems. The Journal of Organic Chemistry,
71, 2434-2444.
9. Bonjoch, J., Diaba, F., Puigbo, G. et al. (2003) A new synthetic entry to the tricyclic skeleton of
FR901483 by palladium-catalysed cyclization of vinyl bromides with ketone enolates. Tetrahe-
dron Letters, 44, 8387-8390.
10. Ono, N., Kamiura, A., Miyake, H. et al. (1985) New synthetic methods. Conjugate addition of
alkyl groups to electron deficient olefins with nitroalkanes as alkyl anion equivalents. The
Journal of Organic Chemistry, 50, 3692-3698.
11. Chung, J.Y.L., Grabowski, E.J.J. and Reider, P.J. (1999) Sequential nitromethane conjugate
addition/elimination-Pd-catalysed allylation of
b
-trifloxy acrylates. Application to carbapenem
synthesis. Organic Letters, 1, 1783-1785.
12. Mamdani, H.T. and Hartley, R.C. (2000) Phosphazene bases and the anionic oxy-Cope
rearrangement. Tetrahedron Letters, 41, 747-749.
13. Corey, E.J. and Kania, R.S. (1996) First enantioselective total synthesis of a naturally occurring
dolabellane. Revision of absolute configuration. Journal of the American Chemical Society, 118,
1229-1230.
14. Blid, J. and Somfai, P. (2003) Lewis acid mediated [2,3]-sigmatropic rearrangement of allylic
ammonium ylides. Tetrahedron Letters, 44, 3195-3162.
 
Search WWH ::




Custom Search