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

Kalmode, Hanuman P. ; Handore, Kishor L. ; Reddy, D. Srinivasa (2017) Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold Journal of Organic Chemistry, 82 (14). pp. 7614-7620. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.7b00794

Related URL: http://dx.doi.org/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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:121924
Deposited On:23 Jul 2021 08:06
Last Modified:23 Jul 2021 08:06

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