Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3
Abstract We describe herein an efficient synthesis of the C1–C9, C11–C19 pyran moiety and C18–C24 core fragments of macrolactin 3. The prominent features of this work include construction of the Z-double bond of the 1,3-(Z,E)-diene system utilizing Horner–Wadsworth–Emmons reaction under Still–Genna...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag KG
2017-03-01
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| Series: | SynOpen |
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| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591844 |
| _version_ | 1818891651221815296 |
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| author | A. Maheshwar Reddy Gowravaram Sabitha |
| author_facet | A. Maheshwar Reddy Gowravaram Sabitha |
| author_sort | A. Maheshwar Reddy |
| collection | DOAJ |
| description | Abstract
We describe herein an efficient synthesis of the C1–C9, C11–C19 pyran moiety and C18–C24 core fragments of macrolactin 3. The prominent features of this work include construction of the Z-double bond of the 1,3-(Z,E)-diene system utilizing Horner–Wadsworth–Emmons reaction under Still–Gennari conditions. A Sharpless asymmetric epoxidation and subsequent epoxide opening under BF3·OEt2 conditions were applied to generate the stereogenic centers at C15 and C16, oxa-Michael addition and Jacobsen resolution facilitate the synthesis of the fragments. |
| first_indexed | 2024-12-19T17:44:12Z |
| format | Article |
| id | doaj.art-6189a0f26a824eb098794c0a94f25617 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-19T17:44:12Z |
| publishDate | 2017-03-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-6189a0f26a824eb098794c0a94f256172022-12-21T20:12:07ZengGeorg Thieme Verlag KGSynOpen2509-93962017-03-0101010166017210.1055/s-0036-1591844Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3A. Maheshwar Reddy0Gowravaram Sabitha1Natural Products Chemistry Division and CSIR-Indian Institute of Chemical TechnologyNatural Products Chemistry Division and CSIR-Indian Institute of Chemical TechnologyAbstract We describe herein an efficient synthesis of the C1–C9, C11–C19 pyran moiety and C18–C24 core fragments of macrolactin 3. The prominent features of this work include construction of the Z-double bond of the 1,3-(Z,E)-diene system utilizing Horner–Wadsworth–Emmons reaction under Still–Gennari conditions. A Sharpless asymmetric epoxidation and subsequent epoxide opening under BF3·OEt2 conditions were applied to generate the stereogenic centers at C15 and C16, oxa-Michael addition and Jacobsen resolution facilitate the synthesis of the fragments.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591844macrolactin 3 tetrahydropyranbf3·oet2 epoxide openingjacobsenoxa-michael d-ribose |
| spellingShingle | A. Maheshwar Reddy Gowravaram Sabitha Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 SynOpen macrolactin 3 tetrahydropyran bf3·oet2 epoxide opening jacobsen oxa-michael d-ribose |
| title | Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 |
| title_full | Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 |
| title_fullStr | Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 |
| title_full_unstemmed | Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 |
| title_short | Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3 |
| title_sort | synthesis of the c1 c9 c11 c19 pyran core and c19 c24 fragments of macrolactin 3 |
| topic | macrolactin 3 tetrahydropyran bf3·oet2 epoxide opening jacobsen oxa-michael d-ribose |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591844 |
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