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Synthesis 2020; 52(14): 2045-2064
DOI: 10.1055/s-0039-1690840
DOI: 10.1055/s-0039-1690840
paper
Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies
Financial assistance from the Science and Engineering Research Board (SERB), New Delhi (EMR/2017/002239) is gratefully acknowledged. P.S., M.T.M., B.P.D., G.M.A., P.S., and S.K.R. thank the Council of Scientific and Industrial Research (CSIR) and the University Grants Commission (UGC) for research fellowships.Further Information
Publication History
Received: 23 December 2019
Accepted after revision: 05 February 2020
Publication Date:
27 March 2020 (online)
Abstract
We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide substrate scope with different indoles. Zerumbone epoxide furnished [5.3.0] and [6.3.0] fused structurally diverse sesquiterpenoids and all other zerumbone derivatives furnished the [6.3.0] fused motifs.
Key words
zerumbone - zerumbone epoxide - zerumbal - zerumbenone - Lewis acid catalysis - cyclization - polycyclic terpenoidsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690840.
- Supporting Information
- CIF File
-
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