The 25th ISHC Congress–Santa Barbara CA Aug 23-28, 2015
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Title:
Rapid Composition of Tricyclic Spiranoid Lactones: Access to Natural and Unexplored Frames
Abstract: (Your abstract must use Normal style and must fit into the box. Do not enter author details)
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.