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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 19
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Original Articles

Degradation of the Side Chain of (−)‐Sclareol: A Very Short Synthesis of nor‐Ambreinolide and Ambrox

A. F. Barrero Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
,
E. J. Alvarez‐Manzaneda Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, SpainCorrespondence[email protected]
,
R. Chahboun Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
&
A. F. Arteaga Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071, Granada, Spain
Pages 3631-3643 | Received 29 Jul 2003, Published online: 10 Jan 2011

Citations (22)

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Efficient N. Ncube, Kgama Mathiba, Lucia H. Steenkamp & Ian A. Dubery. (2022) Gas chromatographic profiling of the biocatalytic conversion of sclareol to ambradiol by Hyphozyma roseoniger. Biocatalysis and Biotransformation 40:4, pages 308-312.
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Articles from other publishers (21)

Ni He, Dong-Fang Li, Hong-Wei Yu & Li-Dan Ye. (2023) Construction of an Artificial Microbial Consortium for Green Production of (−)-Ambroxide. ACS Sustainable Chemistry & Engineering 11:5, pages 1939-1948.
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Yakun Fang, Zilong Wang, Yi Shi, Fan Liu, Junhua Wang, Ting Yang, Yu Xin, Zhenghua Gu & Liang Zhang. (2022) Efficient Biotransformation of Sclareol to Sclareolide by Filobasidium magnum JD1025. Applied Biochemistry and Biotechnology 195:2, pages 1184-1196.
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Kyriaki Gennaiou, Antonios Kelesidis, Maria Kourgiantaki & Alexandros L Zografos. (2023) Combining the best of both worlds: radical-based divergent total synthesis. Beilstein Journal of Organic Chemistry 19, pages 1-26.
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Viktoriia Zubar, Niels Lichtenberger, Mathias Schelwies, Thomas Oeser, A. Stephen K. Hashmi & Thomas Schaub. (2021) Manganese‐Catalyzed Hydrogenation of Sclareolide to Ambradiol. ChemCatChem 14:1.
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Efficient N. Ncube, Lucia Steenkamp & Ian A. Dubery. (2020) Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors. Molecules 25:17, pages 3851.
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Kanyavee Wootitunthipong & James Chickos. (2019) Vaporization enthalpy and vapor pressure of (−) Ambroxide and Galaxolide by correlation gas chromatography. The Journal of Chemical Thermodynamics 129, pages 121-129.
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Joana R. Raimundo, David F. Frazão, Joana L. Domingues, Celestino Quintela-Sabarís, Teresa P. Dentinho, Ofélia Anjos, Marcos Alves & Fernanda Delgado. (2018) Neglected Mediterranean plant species are valuable resources: the example of Cistus ladanifer. Planta 248:6, pages 1351-1364.
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Shasha Zhang, Xia Wang, Jin Hao, Dangdang Li, René Csuk & Shengkun Li. (2018) Expediently Scalable Synthesis and Antifungal Exploration of (+)-Yahazunol and Related Meroterpenoids. Journal of Natural Products 81:9, pages 2010-2017.
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Dangdang Li, Shasha Zhang, Zehua Song, Wei Li, Feng Zhu, Jiwen Zhang & Shengkun Li. (2018) Synthesis and bio-inspired optimization of drimenal: Discovery of chiral drimane fused oxazinones as promising antifungal and antibacterial candidates. European Journal of Medicinal Chemistry 143, pages 558-567.
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Dangdang Li, Shasha Zhang, Zehua Song, Guotong Wang & Shengkun Li. (2017) Bioactivity-guided mixed synthesis accelerate the serendipity in lead optimization: Discovery of fungicidal homodrimanyl amides. European Journal of Medicinal Chemistry 136, pages 114-121.
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Shaoxiang Yang, Hongyu Tian, Baoguo Sun, Yongguo Liu, Yanfeng Hao & Yanyu Lv. (2016) One-pot synthesis of (−)-Ambrox. Scientific Reports 6:1.
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Adam Skiredj, Mehdi A. Beniddir, Laurent Evanno & Erwan Poupon. (2016) Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds. European Journal of Organic Chemistry 2016:17, pages 2954-2958.
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Alejandro Torres, Pilar Gutierrez, Ramón Alvarez-Manzaneda, Rachid Chahboun & Enrique Alvarez-Manzaneda. (2016) Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A. Organic & Biomolecular Chemistry 14:41, pages 9836-9845.
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Dang-Dang Li, Xin-Wei Shi, Qiang-Qiang Lu & Sheng-Kun Li. (2015) Crystal structure of 2-[(1 R ,2 R ,4a S ,8a S )-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]- N -( o -tolyl)acetamide . Acta Crystallographica Section E Crystallographic Communications 71:10, pages o788-o789.
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Niangoran Koissi & James C. Fishbein. (2013) Trapping of a Cross-Link Formed by a Major Purine Adduct of a Metabolite of the Carcinogen N -Nitrosomorpholine by Inorganic and Biological Reductants . Chemical Research in Toxicology 26:5, pages 732-740.
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Christophe Sallaud, Cécile Giacalone, Romy Töpfer, Simon Goepfert, Nicolas Bakaher, Sandrine Rösti & Alain Tissier. (2012) Characterization of two genes for the biosynthesis of the labdane diterpene Z ‐abienol in tobacco ( Nicotiana tabacum) glandular trichomes . The Plant Journal 72:1, pages 1-17.
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Sunisa Suwancharoen, Surachai Pornpakakul & Nongnuj Muangsin. (2012) Synthesis of ent-ambrox® from (−)-nidorellol. Tetrahedron Letters 53:40, pages 5418-5421.
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Alain Tissier. (2012) Glandular trichomes: what comes after expressed sequence tags?. The Plant Journal 70:1, pages 51-68.
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Kiran B. Upar, Sanjay J. Mishra, Shrikant P. Nalawade, Soni A. Singh, Reena P. Khandare & Sujata V. Bhat. (2009) Efficient enantioselective synthesis of (+)-sclareolide and (+)-tetrahydroactinidiolide: chiral LBA-induced biomimetic cyclization. Tetrahedron: Asymmetry 20:14, pages 1637-1640.
Crossref
A. F. Barrero, E. J. Alvarez‐Manzaneda, R. Chahboun & A. F. Arteaga. (2005) Degradation of the Side Chain of (‐)‐Sclareol: A Very Short Synthesis of nor‐Ambreinolide (III) and Ambrox (VI).. ChemInform 36:7.
Crossref
Braulio M. Fraga. (2005) Natural sesquiterpenoids. Natural Product Reports 22:4, pages 465.
Crossref

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