Synthesis 2020; 52(14): 2045-2064
DOI: 10.1055/s-0039-1690840
paper
© Georg Thieme Verlag Stuttgart · New York

Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies

Puthiyaparambath Sharathna
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
b   Academy 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
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
b   Academy 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
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
,
Greeshma Gopalan
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
,
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
,
Radhakrishnan Syam Krishnan
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
,
a   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-19, India
b   Academy of Scientific and Innovative Research (AcSIR), CSIR- Human Resource Development Centre, (CSIR-HRDC) Campus Ghaziabad, Uttar Pradesh- 201 002, India   eMail: radhu2005@gmail.com
› Institutsangaben
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.
Weitere Informationen

Publikationsverlauf

Received: 23. Dezember 2019

Accepted after revision: 05. Februar 2020

Publikationsdatum:
27. März 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.

Supporting Information