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Kalmode HP, Handore KL, Reddy DS. Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold. J Org Chem. 2017;82(14):7614-7620doi: 10.1021/acs.joc.7b00794.
Kalmode, H. P., Handore, K. L., & Reddy, D. S. (2017). Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold. The Journal of organic chemistry, 82(14), 7614-7620. https://doi.org/10.1021/acs.joc.7b00794
Kalmode, Hanuman P, et al. "Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold." The Journal of organic chemistry vol. 82,14 (2017): 7614-7620. doi: https://doi.org/10.1021/acs.joc.7b00794
Kalmode HP, Handore KL, Reddy DS. Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold. J Org Chem. 2017 Jul 21;82(14):7614-7620. doi: 10.1021/acs.joc.7b00794. Epub 2017 Jul 10. PMID: 28636370.
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J Org Chem. 2017 Jul 21;82(14):7614-7620. doi: 10.1021/acs.joc.7b00794. Epub 2017 Jul 10.

Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold.

The Journal of organic chemistry

Hanuman P Kalmode, Kishor L Handore, D Srinivasa Reddy

Affiliations

  1. Division of Organic Chemistry, CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road, Pune 411008, India.
  2. Academy of Scientific and Innovative Research (AcSIR) , 110025, New Delhi, India.

PMID: 28636370 DOI: 10.1021/acs.joc.7b00794

Abstract

Serendipitous findings of an acid mediated skeletal rearrangement of bicyclo-β-ketoester having cyclopropyl ring to access fused tricyclic γ-butyrolactones has been described. This novel transformation has been optimized to 30 mol% p-toluenesulfonic acid (p-TSA) in toluene using Dean-Stark apparatus, where the aldol condensation, cyclopropyl ring opening followed by cyclization took place in a single-pot operation. The resulting tricyclic compounds are interesting chemotype with natural product resemblance and may find useful applications in the future.

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