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Updated: Jul 9, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Divergent Asymmetric Synthesis of Glutinosasins A-E
Xuezhi Li1, Wenjie Fang1, Qian Hu2
1Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou 510641, P. R. China.
Abstract:
We report a divergent asymmetric synthesis of glutinosasins A-E. Glutinosasins A-D represent a novel subfamily of ent-kaurane diterpenoids characterized by their unprecedented 8,14-seco-ent-kaurane scaffold. The synthesis relies on several key steps: (a) a Baran reductive olefin coupling to establish a trans-decalin framework containing a C10 quaternary center; and (b) a Lewis acid-mediated deprotection/retro-Claisen condensation cascade to construct the 8,14-seco-ent-kaurane scaffold. We have developed a stereodivergent strategy for constructing decalin frameworks, where a C7-sp3 substrate delivers a trans-decalin structure, while a C7-sp2 substrate provides a cis-decalin configuration. This approach can be extended to the synthesis of related natural products containing either cis- or trans-decalin motifs.
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