Synthesis of the Ring D-Building Block of (24S)-24-Hydroxy Vitamin D3 from Menthol, I

Natural (—)‐menthol (4) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10. The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24S)‐24‐hydroxy vitamin D3. Th...

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Veröffentlicht in:	Liebigs Annalen der Chemie 1992-09, Vol.1992 (9), p.965-973
Hauptverfasser:	Daniewski, Andrzej Robert, Warchol, Tadeusz
Format:	Artikel
Sprache:	eng
Schlagworte:	(-)-Menthol Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties Vitamin D3
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container_title	Liebigs Annalen der Chemie
container_volume	1992
creator	Daniewski, Andrzej Robert Warchol, Tadeusz
description	Natural (—)‐menthol (4) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10. The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24S)‐24‐hydroxy vitamin D3. The title compound 18 was synthesized also by free‐radical cyclization of enaldehyde 40.
doi_str_mv	10.1002/jlac.1992199201159
format	Article
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The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24S)‐24‐hydroxy vitamin D3. The title compound 18 was synthesized also by free‐radical cyclization of enaldehyde 40.</description><identifier>ISSN: 0170-2041</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/jlac.1992199201159</identifier><identifier>CODEN: LACHDL</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>(-)-Menthol ; Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties ; Vitamin D3</subject><ispartof>Liebigs Annalen der Chemie, 1992-09, Vol.1992 (9), p.965-973</ispartof><rights>Copyright © 1992 WILEY‐VCH Verlag GmbH & Co. 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Chem</addtitle><description>Natural (—)‐menthol (4) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10. The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24S)‐24‐hydroxy vitamin D3. 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Chem</addtitle><date>1992-09-17</date><risdate>1992</risdate><volume>1992</volume><issue>9</issue><spage>965</spage><epage>973</epage><pages>965-973</pages><issn>0170-2041</issn><eissn>1099-0690</eissn><coden>LACHDL</coden><abstract>Natural (—)‐menthol (4) was oxidized to the lactone 9 which was alkylated with allyl bromide to a single product 10. The latter compound was transformed into bromo epoxide 33 which was cyclized with the highly reactive copper to the desired ring D Building block 18 of (24S)‐24‐hydroxy vitamin D3. The title compound 18 was synthesized also by free‐radical cyclization of enaldehyde 40.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/jlac.1992199201159</doi><tpages>9</tpages></addata></record>
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subjects	(-)-Menthol Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties Vitamin D3
title	Synthesis of the Ring D-Building Block of (24S)-24-Hydroxy Vitamin D3 from Menthol, I
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