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Updated: Jul 6, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Diastereoselective allylation-based asymmetric total synthesis of 1,10-seco-guaianolides
Rodney A Fernandes1, Ravikant S Ranjan1
1Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in.
Abstract:
A Cr(II)-mediated Nozaki-Hiyama allylation of aldehydes with functionalized chiral allylbromolactone paved the way to easily access β-hydroxy-aryl/alkyl-α-methylene-γ-butyrolactones in good yields with high diastereoselectivities. A subsequent undemanding translactonization was orchestrated in the efficient first asymmetric total synthesis of two 1,10-seco-guaianolides as a valuable extension of the strategy developed.
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