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. 2017 Dec 12;8:2083. doi: 10.1038/s41467-017-02061-7

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© The Author(s) 2017

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Fig. 5 — Chemical synthesis of (+)-aureol (2), (–)-cyclosmenospongine (5), (–)-mamanuthaquinone (6), and (+)-5-epi-aureol (9). The 3-deoxy-5,6-dehydrodecalin unit 33 was accessed in three steps from the known coupling of 21 and 31. Installation of the C15–C16 carbon–carbon bond was accomplished by ortho-directed lithiation of 34 or 36 and nucleophilic addition to 33. AIBN azobisisobutyronitrile, NaHMDS sodium hexadimethylsilazide, TMEDA N,N,N,N′-tetramethylethylenediamine