Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies

Puthiyaparambath Sharathna; Murugan Thulasi Meenu; Bhandara Purayil Dhanya; Greeshma Gopalan; Parameswaran Sasikumar; Radhakrishnan Syam Krishnan; Kokkuvayil Vasu Radhakrishnan

doi:10.1055/s-0039-1690840

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(14): 2045-2064
DOI: 10.1055/s-0039-1690840

paper

Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies

Puthiyaparambath Sharathna‡

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

^bAcademy of Scientific and Innovative Research (AcSIR), CSIR- Human Resource Development Centre, (CSIR-HRDC) Campus Ghaziabad, Uttar Pradesh- 201 002, India eMail: radhu2005@gmail.com

,

Murugan Thulasi Meenu‡

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

^bAcademy of Scientific and Innovative Research (AcSIR), CSIR- Human Resource Development Centre, (CSIR-HRDC) Campus Ghaziabad, Uttar Pradesh- 201 002, India eMail: radhu2005@gmail.com

,

Bhandara Purayil Dhanya

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

,

Greeshma Gopalan

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

,

Parameswaran Sasikumar

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

,

Radhakrishnan Syam Krishnan

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

,

Kokkuvayil Vasu Radhakrishnan ∗

^aOrganic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India

^bAcademy of Scientific and Innovative Research (AcSIR), CSIR- Human Resource Development Centre, (CSIR-HRDC) Campus Ghaziabad, Uttar Pradesh- 201 002, India eMail: radhu2005@gmail.com

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Abstract

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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 terpenoids

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