Lewis-Acid-Catalyzed Activation of Zerumbone towards Sesquiterpenoid Derivatives: Sustainable Utilization of Abundant Natural Resources for the Synthesis of Chemically Diverse Architectures

A facile Lewis-acid-catalyzed method for the synthesis of structurally diverse sesquiterpenoid derivatives from readily available and abundant 11-membered natural product zerumbone has been developed. Starting from zerumbone, we have developed an efficient cyclization process for the creation of [5....

Full description

Saved in:
Bibliographic Details
Published inAsian journal of organic chemistry Vol. 7; no. 2; pp. 471 - 476
Main Authors Dhanya, Bhandara Purayil, Gopalan, Greeshma, Sasikumar, Parameswaran, Neethu, Sivadas, Meenu, Murugan Thulasi, Sharathna, Puthiyaparambath, John, Jubi, Varughese, Sunil, Sabu, Mamiyil, Dan, Mathew, Radhakrishnan, Kokkuvayil Vasu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.02.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BICYCLIC HYDRAZINES
ASYMMETRIC-SYNTHESIS
3,4-DISUBSTITUTED CYCLOPENTENES
Lewis acids
sesquiterpenoids
FUNCTIONALIZED CYCLOPENTENES
zerumbone
cyclization
INTERRUPTED NAZAROV REACTION
natural products
PENDANT DERIVATIVES
AZABICYCLIC OLEFINS
STEREOSELECTIVE-SYNTHESIS
ALKYLIDENE CYCLOPENTENES
CONJUGATE ADDITION
Online AccessGet more information

Cover

More Information
Summary:A facile Lewis-acid-catalyzed method for the synthesis of structurally diverse sesquiterpenoid derivatives from readily available and abundant 11-membered natural product zerumbone has been developed. Starting from zerumbone, we have developed an efficient cyclization process for the creation of [5.7], [5.8], and [5.8.3] fused-ring systems. This process was exemplified by the selective functionalization of zerumbone; by controlling the conformation of the 11-membered ring, the ring-closing process could be tuned to afford the fused-ring system of choice.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800006