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Updated: Jul 15, 2026

Bimolecular Fluorescence Complementation
Published on: April 15, 2011
Intramolecular silicon-assisted cross-coupling: total synthesis of (+)-brasilenyne
Scott E Denmark1, Shyh-Ming Yang
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Abstract:
The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter and the successful application of the sequential ring closing metathesis/silicon-assisted intramolecular cross-coupling reaction for construction of the oxonin core structure of 1.
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