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Paper | Special issue | Vol 95, No. 2, 2017, pp.894-919
Published online, 13th December, 2016
DOI: 10.3987/COM-16-S(S)58
A Remarkably Useful Sulfur Bridge as Synthetic Lever in an Approach to Javanicin B

Amélie Dion and Claude Spino*

*Département de chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, J1K 2R1, Canada


A concise and efficient synthesis of a non-racemic advanced intermediate to the quassinoid javanicin B is disclosed. The strategy is centred on a triple diene-transmissive Diels-Alder cycloaddition to form the four rings of javanicin B. A sulfur bridge plays several crucial roles allowing an intramolecular cycloaddition to occur with complete stereoselectivity, controlling the stereochemical outcome of another cycloaddition, and transforming into a pivotal electrophile for the introduction of a particularly hindered methyl group.