Ncube, ENSteenkamp, Lucia HDubery, IA2020-12-032020-12-032020-08Ncube, E.N., Steenkamp, L.H. & Dubery, I.A. 2020. Ambrafuran (AmbroxTM) synthesis from natural plant product precursors. Molecules, vol. 25. No. 17, pp. 131420-3049https://www.mdpi.com/1420-3049/25/17/3851https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7504449/doi: 10.3390/molecules25173851https://doi.org/10.3390/molecules25173851http://hdl.handle.net/10204/11684Copyright 2020. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name: 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran.enAmbrafuranFragrancesLabdaneSynthesisTerpenesTerpenoidsArticleNcube, E., Steenkamp, L. H., & Dubery, I. (2020). Ambrafuran (AmbroxTM) synthesis from natural plant product precursors. http://hdl.handle.net/10204/11684Ncube, EN, Lucia H Steenkamp, and IA Dubery "Ambrafuran (AmbroxTM) synthesis from natural plant product precursors." (2020) http://hdl.handle.net/10204/11684Ncube E, Steenkamp LH, Dubery I. Ambrafuran (AmbroxTM) synthesis from natural plant product precursors. 2020; http://hdl.handle.net/10204/11684.TY - Article AU - Ncube, EN AU - Steenkamp, Lucia H AU - Dubery, IA AB - Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name: 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran. DA - 2020-08 DB - ResearchSpace DP - CSIR KW - Ambrafuran KW - Fragrances KW - Labdane KW - Synthesis KW - Terpenes KW - Terpenoids LK - https://researchspace.csir.co.za PY - 2020 SM - 1420-3049 T1 - Ambrafuran (AmbroxTM) synthesis from natural plant product precursors TI - Ambrafuran (AmbroxTM) synthesis from natural plant product precursors UR - http://hdl.handle.net/10204/11684 ER -