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Department of Chemistry
Indian Institute of Technology Delhi

New strategies and methods for the total synthesis of natural products

Dr. Gowrisankar Parthasarathy

Dept. of Organic Chemistry, Leibniz-University of Hannover, Germany

Date : April 18th 2013 (Thursday)
Time : 12:00 noon
Venue: Committee Room, Chemistry Department

My lecture will focus mainly on total/formal/partial syntheses of some structurally challenging, bioactive terpenoids and cycto-toxic marine macrolides. I started my Ph.D work on the synthesis of dysidiolide for which we developed a short and efficient enyne metathesis strategy for the construction of a key intermediate and completed the formal synthesis of dysidiolide. Later, I worked on the synthesis of a novel marine natural product, palmerolide A and we were the first to report a partial synthesis of this highly cytotoxic compound. Subsequently, I contributed significantly to the formal total synthesis of palmerolide A involving 24 longest linear steps. The key features of the synthesis involved the Sharpless epoxidation and Shimizu-non aldol approach to construct the syn aldol moiety, a Julia–Kocienski reaction to construct the diene, and ring-closing metathesis to form the macro cycle. During my post-doctoral work at Purdue University, we developed a pinane based chiral auxiliary for the diastereoselective and enantioselective aldol reaction of 3,3,3-trifluoropropionates, leading to the total synthesis of C6-CF3-dictyostatin. At the University of Geneva, we have reported the first total synthesis of (+)-5-epi-eudesma-4(15)-ene-1ß,6ß-diol by utilizing the Ireland-Claisen rearrangement of glycolate ester and INOC as key steps starting from the known (R)-piperitone. At present (University of Hannover), I have been working on a highly convergent strategy for the total synthesis of omphadiol which we completed the formal synthesis in 10 linear steps involving a selective three component coupling, diasteroselective reduction, FVP and RCM.

Kaliappan, K. P.; Parthasarathy, G. Tetrahedron Lett. 2004, 45, 8207. a) Kaliappan, K. P.; Parthasarathy, G. Synlett, 2007, 1537; b) Parthasarathy, G.; Pujari, S. A.; Kaliappan, K. P. Chem. Eur. J. 2010, 16, 5858; c) Pujari, S. A.; Parthasarathy, G.; Kaliappan. K. P. Chem. Asian J. 2011, 06, 3137. a) Ramachandran, P. V; Parthasarathy, G.; Gagare, P. D. Org. Lett., 2010, 12, 4474; b) Ramachandran, P. V; Parthasarathy, G.; Gagare, P. D. Tetrahedron Lett. 2011, 52, 5359; c) Ramachandran, P. V; Gagare, P. D.; Parthasarathy, G. Tetrahedron Lett. 2011, 52, 6055. Parthasarathy, G.; Besnard, C.; Kündig, E. P. Chem. Commun., 2012, 48, 11241. Unpublished results.

All are cordially invited to attend

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Department of Chemistry, Indian Institute of Technology Delhi