This event has ended. View the official site or create your own event → Check it out
This event has ended. Create your own

For Campus Prearrival Information <click here>
For a PDF of the 2015 Program Materials <click here>
For ALL Abstracts [1-220] in sequential order <click here>
For ALL Authors of the Lecture and Poster Presentations <click here>

View analytic
Tuesday, August 25 • 3:40pm - 4:00pm
[0011] Rapid Composition of Tricyclic Spiranoid Lactones: Access to Natural and Unexplored Frames

Sign up or log in to save this to your schedule and see who's attending!

Limited Capacity seats available

Many important biochemical compounds and drugs of natural origin contain tricyclic spirofuranone ring structures. Analysis of their molecular frames shows a compacted carbon skeleton with angularly fused tricycles of different oxidation states in each of the rings, which together present a real synthetic challenge.

Based on the remarkable core structure similarities among the natural products, we designed a rapid and practical collective synthesis strategy of complex functionalized natural and never-before explored frames. We devised a general and common synthesis of phylogenetically and structurally different tricyclic angularly fused systems via controlled cyclizations of simple key precursors. The novel strategy is short, regio- and stereoselective, and offers the possibility to access a broad spectrum of quaternary carbon-centered spiranoid lactone-based structures. Readily accessible key molecules, which are of lesser complexity than the target natural products, were elaborated by simple synthetic sequences. These yield a broad spectrum of spiranoid lactones of varying complexity.

Only a few of the naturally occurring ring fusion combination sets (mostly five- or six-membered rings) across a broad spectrum of the angularly fused spiranoid lactones are known to exist. Other combinations are extremely rare or do not exist at all. Our methodology enables us to produce new variations of angularly fused structures, providing access to a wide range of compounds that have never before been available and observed. These compounds closely resemble common natural scaffolds and carry potential for becoming valuable drugs/therapeutic agents.

We believe that novel concept will reshape the idea of spiranoid lactone moieties as building blocks in multistep synthesis, thus enabling completely innovative retrosynthetic analyses. Importantly, the application of the invented strategy to easily accessible building blocks will allow for the straightforward preparation of complex systems.


ST Lecturers
avatar for Dmitry Tsvelikhovsky

Dmitry Tsvelikhovsky

Ph.D. SENIOR LECTURER, Hebrew University of Jerusalem
Academic Secretary of MCS-ICS | Medicinal Chemistry Section of the Israel Chemical Society | | Laboratory of Organic Synthesis and Methodology | Institute for Drug Research, | School of Pharmacy, R 416-a, | Faculty of Medicine, Campus Ein Karem | The Hebrew University of Jerusalem | Jerusalem 91120, ISRAEL

Tuesday August 25, 2015 3:40pm - 4:00pm
Corwin East