Total Synthesis and Stereochemical Assignment of Myriaporones 1, 3, and 4
Two stereoselective aldol reactions, a nitrile oxide cycloaddition, and a stereoselective late‐stage epoxidation were key steps in the total synthesis of myriaporones 1, 3, and 4 (see scheme). The synthesis allowed the unambiguous assignment of stereogenic centers not previously assigned for these c...
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| Published in | Angewandte Chemie (International ed.) Vol. 43; no. 13; pp. 1728 - 1730 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
19.03.2004
WILEY‐VCH Verlag Wiley |
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| Abstract | Two stereoselective aldol reactions, a nitrile oxide cycloaddition, and a stereoselective late‐stage epoxidation were key steps in the total synthesis of myriaporones 1, 3, and 4 (see scheme). The synthesis allowed the unambiguous assignment of stereogenic centers not previously assigned for these compounds. |
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| AbstractList | Two stereoselective aldol reactions, a nitrile oxide cycloaddition, and a stereoselective late‐stage epoxidation were key steps in the total synthesis of myriaporones 1, 3, and 4 (see scheme). The synthesis allowed the unambiguous assignment of stereogenic centers not previously assigned for these compounds. |
| Author | Fleming, Kristen N. Taylor, Richard E. |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15038050$$D View this record in MEDLINE/PubMed |
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| Keywords | aldol reaction SECO-ACID EFFICIENT MACROLACTONIZATION diastereoselectivity TEDANOLIDE ALCOHOLS natural products DIVERGENT APPROACH epoxidation 18-MEMBERED ANTITUMOR MACROLIDE FRAGMENT INTERMEDIATE total synthesis STEREOSELECTIVE-SYNTHESIS |
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| Notes | ark:/67375/WNG-W8JZZVZF-W istex:B0B4A66B569FB172B72FD9CCB626E0DB6C578467 ArticleID:ANIE200353348 Support was provided by the National Cancer Institute/National Institutes of Health (CA81128). K.N.F. thanks the University of Notre Dame for support through a J. Peter Grace Prize Fellowship and Searle Fellowship. Professor Kenneth Rinehart is acknowledged for providing spectra of authentic material. Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| SubjectTerms | aldol reaction Alkenes - chemical synthesis Alkenes - chemistry Chemistry Chemistry, Multidisciplinary diastereoselectivity epoxidation Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Molecular Conformation natural products Physical Sciences Pyrans - chemical synthesis Pyrans - chemistry Science & Technology Stereoisomerism total synthesis |
| Title | Total Synthesis and Stereochemical Assignment of Myriaporones 1, 3, and 4 |
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