Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23-Dihydroavermectin B1b Aglycone
The synthesis of several configurationally defined hydroxymilbemycin derivatives is described. One of these allylic alcohols is the known 5‐O‐[(tert‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐O‐[(tert‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B1b, aglycone; 15D), the synthesis of which re...
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| Veröffentlicht in: | Helvetica chimica acta 1990-10, Vol.73 (7), p.1905-1917 |
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| container_end_page | 1917 |
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| container_issue | 7 |
| container_start_page | 1905 |
| container_title | Helvetica chimica acta |
| container_volume | 73 |
| creator | Frei, Bruno Huxley, Philip Maienfisch, Peter Mereyala, Hari Babu Rist, Günther O'Sullivan, Anthony C. |
| description | The synthesis of several configurationally defined hydroxymilbemycin derivatives is described. One of these allylic alcohols is the known 5‐O‐[(tert‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐O‐[(tert‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B1b, aglycone; 15D), the synthesis of which represents LI conversion of the milbemycin to the avermectin series of natural products. The configurations at C(13), C(14), and C(15) of the new milbemycin derivatives were determined by NMR experiments and force‐field calculations. |
| doi_str_mv | 10.1002/hlca.19900730713 |
| format | Article |
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One of these allylic alcohols is the known 5‐O‐[(tert‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐O‐[(tert‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B1b, aglycone; 15D), the synthesis of which represents LI conversion of the milbemycin to the avermectin series of natural products. The configurations at C(13), C(14), and C(15) of the new milbemycin derivatives were determined by NMR experiments and force‐field calculations.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19900730713</identifier><identifier>CODEN: HCACAV</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Helvetica chimica acta, 1990-10, Vol.73 (7), p.1905-1917</ispartof><rights>Copyright © 1990 Verlag GmbH & Co. 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One of these allylic alcohols is the known 5‐O‐[(tert‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐O‐[(tert‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B1b, aglycone; 15D), the synthesis of which represents LI conversion of the milbemycin to the avermectin series of natural products. The configurations at C(13), C(14), and C(15) of the new milbemycin derivatives were determined by NMR experiments and force‐field calculations.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><recordid>eNpNkM9PwjAYhhujiYjePfbizWF_bOt68ICgDIN6gERvTdd1UN060g5k_70jGCX5kjdfvuf9Dg8A1xgNMELkblUqOcCcI8QoYpiegB6OCAlIzKJT0EMIJwHC_OMcXHj_iRDqUNYD63lrm5X2xkNpcziqbWGWGycbU1tYF3BeVxqmbe7qXVuZMtNVq4yFY-3MtoO22sOpVeUmN3YJCbklNBib1Z6XW-0qrZqOfsAZHC7LVtVWX4KzQpZeX_1mH8yfHhejNJi9Taaj4SwwNMQ0iCJKeFhEOEGsGyZjqgglGctJjnVcsKjIw6RLTLiOOeUs5AnLSIQyFWe0D24OX9fSK1kWTlplvFg7U0nXCsxpgkgSdtz9gfs2pW7_70jspYq9VHEkVaSz0fBo7_rBoW98o3d_fem-RMwoi8T760SwxTt5Hr9wkdIfPuF9Rg</recordid><startdate>19901031</startdate><enddate>19901031</enddate><creator>Frei, Bruno</creator><creator>Huxley, Philip</creator><creator>Maienfisch, Peter</creator><creator>Mereyala, Hari Babu</creator><creator>Rist, Günther</creator><creator>O'Sullivan, Anthony C.</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope></search><sort><creationdate>19901031</creationdate><title>Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23-Dihydroavermectin B1b Aglycone</title><author>Frei, Bruno ; Huxley, Philip ; Maienfisch, Peter ; Mereyala, Hari Babu ; Rist, Günther ; O'Sullivan, Anthony C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i3413-553294f518078077a63c232b7d2d1e6f75fd486f7129e693974987b250bc6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Frei, Bruno</creatorcontrib><creatorcontrib>Huxley, Philip</creatorcontrib><creatorcontrib>Maienfisch, Peter</creatorcontrib><creatorcontrib>Mereyala, Hari Babu</creatorcontrib><creatorcontrib>Rist, Günther</creatorcontrib><creatorcontrib>O'Sullivan, Anthony C.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Frei, Bruno</au><au>Huxley, Philip</au><au>Maienfisch, Peter</au><au>Mereyala, Hari Babu</au><au>Rist, Günther</au><au>O'Sullivan, Anthony C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23-Dihydroavermectin B1b Aglycone</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1990-10-31</date><risdate>1990</risdate><volume>73</volume><issue>7</issue><spage>1905</spage><epage>1917</epage><pages>1905-1917</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><coden>HCACAV</coden><abstract>The synthesis of several configurationally defined hydroxymilbemycin derivatives is described. One of these allylic alcohols is the known 5‐O‐[(tert‐butyl)dimethylsilyl]‐13α‐hydroxymilbemycin D (= 5‐O‐[(tert‐butyl)‐dimethylsilyl]‐22,23‐dihydroavermectin B1b, aglycone; 15D), the synthesis of which represents LI conversion of the milbemycin to the avermectin series of natural products. The configurations at C(13), C(14), and C(15) of the new milbemycin derivatives were determined by NMR experiments and force‐field calculations.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19900730713</doi><tpages>13</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23-Dihydroavermectin B1b Aglycone |
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