Asymmetric Synthesis of 3,3′-Pyrrolidonyl Spirooxindole-5′-Carboxylic Ester from l-Tryptophan

Dedicated to Professor H. Ila on her 80^th birthday

Abstract

A highly efficient, multi-gram scale asymmetric synthesis of 3,3′-pyrrolidonyl spirooxindole-5′-carboxylic ester, which could be a potential precursor for the synthesis of cyanogramide, is accomplished from commercially available l-1-methyltryptophan in two pots. Fluoride-promoted desilylative spiro-cyclization of (semi) in situ generated isocyanate derived from l-1-methyltryptophan is the key reaction. Further, a variety of arene-substituted 3,3′-pyrrolidonyl spirooxindole-5′-carboxylxic acid esters were synthesized by late stage functionalization of easily accessible 3,3′-pyrrolidonyl spirooxindole-5′-carboxylic ester.

Key words

spirooxindole - asymmetric synthesis - fluoride-promoted - desilylative - spirocyclization - tryptophan - cyanogramide - 3,3′-pyrrolidonyl spirooxindole

Publication History

Received: 17 August 2024

Accepted after revision: 16 October 2024

Accepted Manuscript online:
16 October 2024

Article published online:
12 November 2024

• References

• 1 Department of Chemistry, The University of Utah, Salt Lake City, UT 84112, USA.
• 2 Department of Pharmaceutical Sciences, University of Kentucky, KY 40536, USA.

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