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. 2019 Jun 17;9:8656. doi: 10.1038/s41598-019-45001-9

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© The Author(s) 2019

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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Chemical structures referenced in this work and the scale-up strategy. (a) Chemical structures of halichondrin B, norhalichondrin B, C52-halichondrin-B alcohol, and C52-halichondrin-B amine/E7130. (b) The strategy for scale-up. The previous synthesis relied on a C38-C39 bond formation strategy. The new synthesis relies on a C37-C38 bond formation strategy. The latter provided 19.5 g of C52-halichondrin-B alcohol with 99.84% purity. Fifteen grams of this compound was used to synthesize 11.5 g of E7130 with 99.81% purity as the first GMP batch (92 overall steps).