Total Synthesis of (+)-Asteltoxin

A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner−Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-05, Vol.125 (18), p.5415-5421
Main Authors: Eom, Khee Dong, Raman, J. Venkat, Kim, Heejin, Cha, Jin Kun
Format: Article
Language:English
Subjects:
Aspergillus - chemistry
Biological and medical sciences
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Microbiology
Morphology, structure, chemical composition
Mycology
Mycotoxins - chemical synthesis
Organic chemistry
Preparations and properties
Pyrones - chemical synthesis
Stereoisomerism
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Summary:A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner−Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja034332q