title: Stereo- and Regioselective Synthesis of Tricyclic Spirolactones by Diastereoisomeric Differentiation of a Collective Key Precursor.
abstract: A general, parallel, and collective synthesis of 5/5/5- and 5/5/6-ring fusion topologies of tricyclic spiranoid lactones through the controlled cyclizations of easily accessible, common key precursors is described. The rapid composition of key cycloalkyl methylene precursors yielded an assembly of bicyclic diastereoisomeric iodolactones, which were individually converted into a wide range of tricyclic, angularly fused spiranoid lactones in a regioselective and stereodirected fashion through the diastereoisomeric differentiation of a collective key precursor. The critical stereochemical assignment of the bicyclic starting materials, as well as the tricyclic targets, was confirmed by X-ray crystal structure determination.
authors.affiliation: The Institute for Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, 91120, Israel.
authors.forename: Viviana
authors.initials: V
authors.lastname: Valerio
authors.affiliation: The Institute for Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, 91120, Israel.
authors.forename: Yelena
authors.initials: Y
authors.lastname: Mostinski
authors.affiliation: The Institute for Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, 91120, Israel.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Kotikalapudi
authors.affiliation: The Institute for Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, 91120, Israel. dmitryt@ekmd.huji.ac.il.
authors.forename: Dmitry
authors.identifier: http://orcid.org/0000-0002-1581-5291
authors.initials: D
authors.lastname: Tsvelikhovsky
keywords: cyclization; diastereoselectivity; lactones; regioselectivity; spiro compounds