Reagent-controlled regiodivergent ring expansions of steroids
dc.contributor.author | Charaschanya, Manwika | |
dc.contributor.author | Aubé, Jeffrey | |
dc.date.accessioned | 2018-06-13T17:53:01Z | |
dc.date.available | 2018-06-13T17:53:01Z | |
dc.date.issued | 2018-03-05 | |
dc.identifier.citation | Charaschanya, M., & Aubé, J. (2018). Reagent-controlled regiodivergent ring expansions of steroids. Nature Communications, 9, 934. http://doi.org/10.1038/s41467-018-03248-2 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/26506 | |
dc.description.abstract | Ring expansion provides a powerful way of introducing a heteroatom substituent into a carbocyclic framework. However, such reactions are often limited by the tendency of a given substrate to afford only one of the two rearrangement products or fail to achieve high selectivity at all. These limitations are particularly acute when seeking to carry out late-stage functionalization of natural products as starting points in drug discovery. In this work, we present a stereoelectronically controlled ring expansion sequence towards selective and flexible access to complementary ring systems derived from common steroidal substrates. Chemical diversification of the reaction intermediate affords over 100 isomerically pure analogs with spatial and functional diversity. This regiodivergent rearrangement, and the concept of using chiral reagents to affect regiocontrol in chiral natural products, should be broadly applicable to late-stage natural product diversification programs. | en_US |
dc.publisher | Nature Publishing Group | en_US |
dc.rights | Copyright © 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/. | en_US |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | en_US |
dc.title | Reagent-controlled regiodivergent ring expansions of steroids | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Charaschanya, Manwika | |
kusw.kudepartment | Medicinal Chemistry | en_US |
dc.identifier.doi | 10.1038/s41467-018-03248-2 | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-1049-5767 | |
kusw.oaversion | Scholarly/refereed, publisher version | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess | en_US |
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Except where otherwise noted, this item's license is described as: Copyright © 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/.