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 inAngewandte Chemie (International ed.) Vol. 43; no. 13; pp. 1728 - 1730
Main Authors Fleming, Kristen N., Taylor, Richard E.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 19.03.2004
WILEY‐VCH Verlag
Wiley
Subjects
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
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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Summary: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.
Bibliography: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.
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NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353348