NDLI: Collective Total Synthesis of Englerin A and B, Orientalol E and F, and Oxyphyllol: Application of the Organocatalytic [4+3] Cycloaddition Reaction

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Collective Total Synthesis of Englerin A and B, Orientalol E and F, and Oxyphyllol: Application of the Organocatalytic [4+3] Cycloaddition Reaction

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Collective Total Synthesis of Englerin A and B, Orientalol E and F, and Oxyphyllol: Application of the Organocatalytic [4+3] Cycloaddition Reaction

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Shang, Yong-jia Lin, Guo-qiang Sun, Bing-feng Chen, Shu-guang Wang, Jie
Description	Author Affiliation: Wang J ( CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai, Institute of Organic Chemistry, 345 Lingling Road, 200032, China.)
Abstract	The concise collective total synthesis of englerin A and B, orientalol E and F, and oxyphyllol has been accomplished in 10–15 steps, with the total synthesis of orientalol E and oxyphyllol being achieved for the first time. The success obtained was enabled by the realization of the [4+3] cycloaddition reaction of 9 and 10. Other features of the synthesis include 1) the intramolecular Heck reaction to access the azulene core, 2) the $epoxidation–S_{N}2′$ reduction sequence to access the allylic alcohol, 3) the efficient regioselective and stereoselective formal hydration of the bridging CC bond in the synthesis of englerins, and 4) the late-stage chemo- and stereoselective CH oxidation in the synthesis of orientalol E. The total synthesis of these natural products has enabled the structural revision of oxyphyllol and established the absolute stereochemical features of the organocatalytic [4+3] cycloaddition reaction. The identification of 5 as the natural product oxyphyllol, the success in converting 5 to orientalol E, along with the fact that englerins and oxyphyllol were isolated from plants of the same genus Phyllanthus gives support to our proposed biosynthetic pathways. This work may enable detailed biological evaluations of these natural products and their analogues and derivatives, especially of their potential in the fight against renal cell carcinoma (RCC).
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	7
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-02-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Antineoplastic Agents, Phytogenic Chemical Synthesis Biological Products Carcinoma, Renal Cell Chemistry Drug Therapy Sesquiterpenes, Guaiane Catalysis Cyclization Cycloaddition Reaction Oxidation-Reduction Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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