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. 2018 Mar 16;9:1105. doi: 10.1038/s41467-018-03443-1

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© The Author(s) 2018

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. 2 — Gram-scale synthesis of (±)-CFA. Five step synthesis of aldehyde 7, followed by syn-selective room temperature aldol addition with ester 8. Aldol addition product 9 undergoes dehydration and IMDA cyclization of the resultant triene at elevated temperature. DHP: dihydropyran, DMSO: dimethyl sulfoxide, PPTS: pyridinium p-toluenesulfonate, DIPEA: N,N-diisopropylethylamine, DIC: N,N’-diisopropylcarbodiimide, PTSA: p-toluenesulfonic acid, PDC: pyridinium dichromate