Callipeltoside A: Assignment of Absolute and Relative Configuration by Total Synthesis

A series of highly stereospecific reactions were used in the total synthesis of callipeltoside A (1), thus allowing the assignment of its absolute and relative configuration. a) Schmidt glycosylation, b) Ru Alder–ene coupling, c) Emmons–Wadsworth–Horner olefination, d) chiral auxiliary directed alky...

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Published inAngewandte Chemie International Edition Vol. 41; no. 5; pp. 841 - 843
Main Authors Trost, Barry M., Dirat, Olivier, Gunzner, Janet L.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.03.2002
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
asymmetric synthesis
Chemistry
Chemistry, Multidisciplinary
configuration determination
Macrolides
natural products
Optical Rotation
Physical Sciences
Porifera - chemistry
Rhamnose - chemistry
Science & Technology
Stereoisomerism
total synthesis
FRAGMENT
natural products
configuration determination
asymmetric synthesis
total synthesis
MACROLIDE
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Summary:A series of highly stereospecific reactions were used in the total synthesis of callipeltoside A (1), thus allowing the assignment of its absolute and relative configuration. a) Schmidt glycosylation, b) Ru Alder–ene coupling, c) Emmons–Wadsworth–Horner olefination, d) chiral auxiliary directed alkylation, e) asymmetric allylic Pd alkylation.
Bibliography:istex:CE12BFE893FC297E8F3AE6D6931AF78C6233DC89
ark:/67375/WNG-3X3GH4W8-L
ArticleID:ANIE841
We thank the National Science Foundation and the National Institutes of Health for their generous support of our programs. OD was supported in part by a fellowship from the Association pour la Recherche contre le Cancer (ARC). J.L.G. was supported in part by a NIH postdoctoral fellowship from the National Cancer Institute. Mass spectra were provided by the Mass Spectroscopy Facility at the University of California, San Francisco supported by the NIH Division of Research Resources, and the Mass Spectrometry Facility at University of California, Irvine. We thank Dr. John Greaves of the latter facility for his assistance.
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ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020301)41:5<841::AID-ANIE841>3.0.CO;2-2