[et_pb_section fb_built=”1″ admin_label=”Class Details Section” _builder_version=”4.16″ background_color=”#ffffff” custom_padding=”0px||0px|” global_colors_info=”{}”][et_pb_row _builder_version=”4.16″ custom_padding=”||5px|||” global_colors_info=”{}”][et_pb_column type=”4_4″ _builder_version=”4.16″ custom_padding=”|||” global_colors_info=”{}” custom_padding__hover=”|||”][et_pb_text _builder_version=”4.16″ custom_margin=”||15px|||” global_colors_info=”{}”]<\/p>\n
[\/et_pb_text][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”4.16″ global_colors_info=”{}”][et_pb_column type=”4_4″ _builder_version=”4.16″ custom_padding=”|||” global_colors_info=”{}” custom_padding__hover=”|||”][et_pb_tabs active_tab_background_color=”#109dc0″ inactive_tab_background_color=”#109dc0″ active_tab_text_color=”#ffffff” _builder_version=”4.16″ tab_text_color=”#ffffff” body_font=”||||||||” tab_font=”||||||||” tab_line_height=”1.8em” global_colors_info=”{}”][et_pb_tab title=”\u00bb” _builder_version=”4.16″ global_colors_info=”{}”][\/et_pb_tab][et_pb_tab title=”ABSTRACT” _builder_version=”4.16″ body_font=”||||||||” tab_font=”||||||||” global_colors_info=”{}”]4-Formyl estrone was synthesized in overall good yield in three steps starting from estrone. This was achieved by conducting an electrophilic aromatic substitution reaction using formaldehyde, triethylamine, and MgCl2 on 2-tert-butyl estrone, which was readily prepared in 96% yield from estrone using tert-butyl alcohol and BF3OEt2. The tert-butyl group acted as a positional protecting group to prevent reaction at the 2-position. The tert-butyl group was readily removed in good yield using AlCl3 in dichloromethane\/CH3NO2. To our knowledge, this represents the first use of a positional protecting group for the synthesis of a C-4-modified estrogen. 4-Formyl estrone was used as a common precursor to obtain a variety of other C-4 modified estrogens in very high yields such as 4-methylestrone and 4-hydroxymethylestrone as well as the novel estrogen 4-carboxyestrone. The syntheses of 4-formyl, -methyl-, and -hydroxymethyl estrone represent dramatic improvements over previously reported syntheses of these compounds. [\/et_pb_tab][et_pb_tab title=”PDF” _builder_version=”4.16″ link_option_url=”https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo7017075″ link_option_url_new_window=”on” global_colors_info=”{}”]Download PDF »[\/et_pb_tab][et_pb_tab title=”SUPPORTING INFORMATION” _builder_version=”4.16″ link_option_url=”https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo7017075″ global_colors_info=”{}”]View on PubMed »[\/et_pb_tab][\/et_pb_tabs][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”4.16″ global_colors_info=”{}”][et_pb_column type=”4_4″ _builder_version=”4.16″ custom_padding=”|||” global_colors_info=”{}” custom_padding__hover=”|||”][et_pb_gallery gallery_ids=”2236″ fullwidth=”on” _builder_version=”4.16″ global_colors_info=”{}”][\/et_pb_gallery][\/et_pb_column][\/et_pb_row][et_pb_row _builder_version=”4.16″ global_colors_info=”{}”][et_pb_column type=”4_4″ _builder_version=”4.16″ custom_padding=”|||” global_colors_info=”{}” custom_padding__hover=”|||”][et_pb_text _builder_version=”4.16″ global_colors_info=”{}”]<\/p>\n
Liu, Y.;\u00a0Kim, B.<\/u>; Taylor, S. D. J. Org. Chem.\u00a02007<\/b>, 72, 8824\u20138830.<\/p>\n
[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"
1.\u00a0Synthesis of 4-Formyl Estrone Using a Positional Protecting Group and Its Conversion to Other C-4-Substituted Estrogens4-Formyl estrone was synthesized in overall good yield in three steps starting from estrone. This was achieved by conducting an electrophilic aromatic substitution reaction using formaldehyde, triethylamine, and MgCl2 on 2-tert-butyl estrone, which was readily prepared in 96% yield from […]<\/p>\n","protected":false},"author":4,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"","_et_gb_content_width":"","footnotes":""},"categories":[13,12],"tags":[],"class_list":["post-2234","post","type-post","status-publish","format-standard","hentry","category-prior-to-clemson","category-synthesis"],"_links":{"self":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2234","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/comments?post=2234"}],"version-history":[{"count":0,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/posts\/2234\/revisions"}],"wp:attachment":[{"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/media?parent=2234"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/categories?post=2234"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/scienceweb.clemson.edu\/kimgroup\/wp-json\/wp\/v2\/tags?post=2234"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}