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Updated: Mar 28, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Enantioselective Total Synthesis of (+)-Steenkrotin A and Determination of Its Absolute Configuration
Saiyong Pan1, Beiling Gao1, Jialei Hu1
1Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou, 310058, P.R. China.
Abstract:
The first enantioselective total synthesis of (+)-steenkrotin A has been achieved in 18 steps and 4.2 % overall yield. The key features of the strategy entail a Rh-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction, two sequential SmI2 -mediated Ueno-Stork and ketyl-olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol process with inversion of the relative configuration at the C7 position. The absolute configuration of (+)-steenkrotin A was determined based on the stepwise construction of the stereocenters during the total synthesis.
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