Total Synthesis of Bioactive Lactones: Prelactone E, epi-Prelactones V, E, Nonenolides (Z-isomers) and Stagonolide E
Abstract
Thesis is structured in three different parts. The first part is dedicated to the total synthesis of the Z-isomers of nonenolide and desmethyl nonenolide using RCM and Yamaguchi cyclization reactions. The second part discusses the stereoselective total synthesis of stagonolide E. This synthetic strategy involves jacobsen’s kinetic resolution, sharpless epoxidation, Stille-Gennari and Yamaguchi lactonization reactions. Finally the third part deals with a general synthetic approach for the synthesis of b-hydroxy-d-lactones: asymmetric total synthesis of prelactone E and epi-prelactones V and E using Evans aldol reaction as the key step.
Keywords
Full Text:
PDFReferences
S. Hanessian. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: Oxford, 1983.
J. W. Scott. In Asymmetric Synthesis; J. D. Morrison, J. W. Scott, Eds.; Academic Press: New York, 1984, 4, 1–226.
K. Mori. Synthesis of optically active pheromones. Tetrahedron 1989, 45, 3233–3298.
H. Kotsuki, A. Miyazaki, M. Ochi. A new enantioselective synthesis of (4S,5S)-5-(N-Boc)-amino-6-cyclohexyl-4-hydroxy-hexanoic acid lactone, a hydoxyethylene dipeptide isostere precursor. Tetrahedron Lett. 1991, 32, 4503–4504.
S. S. C. Koch, A. R. Chamberli. Enantioselective preparation of β-alkyl-γ-butyrolactones from functionalized ketene Dithioacetals. Journal of Organic Chemistry 1993, 58, 2725–2737.
D. Buisson, R. Azerad. A chemoenzymatic preparation of both enantiomers of ω-hydroxymethyl-substituted lactones. Tetrahedron: Asymmetry 1996, 7, 9–12.
W. H. Pearson, E. J. Hemre. A Practical Synthesis of (-)-Swainsonine. Journal of Organic Chemistry 1996, 61, 7217–7221.
E. Warmerdam, I. Tranoy, B. Renoux, J. P. Gesson. Study of butyrolactones related to sub-type 3 annonaceous acetogenins. Structure revision of itrabin, jetein, laherradurin and otivarin. Tetrahedron Lett. 1998, 39, 8077–8080.
D._Hagen. In The Polyketide Metabolites; O_Hagen, D.,Ed.; Ellis Harwood: New York, 1991; pp 116–137.
G. Sabitha, K. Sudhakar, N. M. Reddy, M. Rajkumar, J. S. Yadav. Chelation-controlled reduction: an enantioselective synthesis of (−)- tarchonanthuslactone. Tetrahedron Lett. 2005, 46, 6567–6570.
G. Sabitha, F. Narjis, R. Swapna, J. S. Yadav. Asymmetric Total Syntheses of (R)-(-)-Argentilactone and (S)-5-Hexadecanolide. Synthesis 2006, 17, 2879–2884.
G. Sabitha, E. V. Reddy, K. Yadagiri, J. S. Yadav. Total synthesis of insect pheromones (R)-4-dodecanolide and (S)-5- hexadecanolide. Synthesis 2006, 19, 3270–3274.
G. Sabitha, K. Sudhakar, J. S. Yadav. Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)- (+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain. Tetrahedron Lett. 2006, 47, 8599–8602.
G. Sabitha, V. Bhaskar, J. S. Yadav. The first asymmetric total synthesis of (R)-tuberolactone, (S)-jasmine lactone and (R)-δ- Decalactone. Tetrahedron Lett. 2006, 47, 8179–8181.
G. Sabitha, R. Swapna, E. V. Reddy, J. S. Yadav. Synthesis of (-)-(5R,6S)-6-Acetoxyhexadecanolide, a Mosquito Oviposition Attractant¬ Pheromone of Culex pipiens fatigans Synthesis 2006, 24, 4242–4246.
G. Sabitha, M. Bhikshapathi, J. S. Yadav. Radical Cyclization Route to the Stereoselective Synthesis of (+)-trans-Cognac Lactone and (+)-trans-Aerangis Lactone. Synth. Commun. 2007, 37, 559–567.
G. Sabitha, K. Yadagiri, J. S. Yadav. Synthesis of the Janus integer pheromone (4R,9Z)-9-octadecen-4-olide. Tetrahedron Lett. 2007, 48, 1651–1652.
G. Sabitha, K. Yadagiri, J. S. Yadav. A short and efficient synthesis of renealtins A and B. Tetrahedron Lett. 2007, 48, 8065–8068.
G. Sabitha, V. Bhaskar, S. Siva sankara Reddy, J. S. Yadav. Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone. Tetrahedron 2008, 64, 10207–10213.
G. Sabitha, P. Padmaja, K. Sudhakar, J. S. Yadav. Total synthesis of z-isomers of nonenolide and desmethyl nonenolide. Tetrahedron Asymmetry 2009, 20, 1330–1336.
G. Sabitha, P. Padmaja, P. Narayana Reddy, Surender Singh Jadav, J. S. Yadav. Stereoselective total synthesis of stagonolide E. Tetrahedron Letters 2010, 51, 6166–6168.
G. Sabitha, P. Padmaja, K. Bhaskar Reddy, J. S. Yadav. A general synthetic approach for the synthesis of β-hydroxy-δ-lactones: asymmetric total synthesis of prelactones and epi-prelactones V and E. Tetrahedron Letters 2008, 49, 919–922.
ISSN 2347 – 8853
Indexed in: