Total Synthesis of Phorboxazole B

Challenge met: In the synthesis of phorboxazole B, a highly efficient hetero‐Diels–Alder reaction was used to construct the key C33–C39 linchpin, allowing for the completion of the C18–C46 fragment (see picture). Coupling with a suitable C3–C17 partner was followed by late‐stage formation of the oxa...

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Published inAngewandte Chemie (International ed.) Vol. 46; no. 5; pp. 769 - 772
Main Authors Lucas, Brian S., Gopalsamuthiram, Vijayagopal, Burke, Steven D.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cycloaddition
cyclodehydration
natural products
Physical Sciences
Science & Technology
symmetry
total synthesis
HIGHLY CONVERGENT
SEGMENT
ANALOGS
DIELS-ALDER REACTION
DIENE
ALPHA-ALKOXY ALDEHYDES
MARINE SPONGE
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Summary:Challenge met: In the synthesis of phorboxazole B, a highly efficient hetero‐Diels–Alder reaction was used to construct the key C33–C39 linchpin, allowing for the completion of the C18–C46 fragment (see picture). Coupling with a suitable C3–C17 partner was followed by late‐stage formation of the oxazole unit, macrocyclization, and deprotection to afford synthetic phorboxazole B.
Bibliography:NIH - No. CA108488; No. CA74394
ark:/67375/WNG-KDQHJVV2-T
The NIH (grants CA108488 and CA74394) graciously funded this research. We thank M. Dodge, L. Wysocki, J. Schuster, L. Boyle, L. Luther, and L. Konkel for providing starting materials crucial to this work. We are grateful to Dr. I. Guzei for the X-ray crystal structure determination of 19. Professors C. J. Forsyth (University of Minnesota) and D. R. Williams (Indiana University) are acknowledged for helpful discussions regarding the hydrolysis of 39.
ArticleID:ANIE200603656
istex:E1F11FF2BE1DA65337FDF7BD467C2BD613F71391
19
Professors C. J. Forsyth (University of Minnesota) and D. R. Williams (Indiana University) are acknowledged for helpful discussions regarding the hydrolysis of
The NIH (grants CA108488 and CA74394) graciously funded this research. We thank M. Dodge, L. Wysocki, J. Schuster, L. Boyle, L. Luther, and L. Konkel for providing starting materials crucial to this work. We are grateful to Dr. I. Guzei for the X‐ray crystal structure determination of
39
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Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603656