NDLI: Studies of stereocontrolled allylation reactions for the total synthesis of phorboxazole A

Content Provider	PubMed Central
Author	Williams, David R. Kiryanov, Andre A. Emde, Ulrich Clark, Michael P. Berliner, Martin A. Reeves, Jonathan T.
Copyright Year	2004
Abstract	A highly convergent total synthesis of the potent anticancer agent (+)-phorboxazole A (1) is accomplished. Four components (3–6) are assembled with considerations for control of absolute and relative stereochemistry. Iterative asymmetric allylation methodology addresses key stereochemical features in the preparation of the 2,6-cis- and 2,6-trans-tetrahydropyranyl rings of the C3–C19 component (3). The stereocontrolled asymmetric allylation process is also used for development of the C28–C41 fragment (4). Novel Barbier coupling reactions of α-iodomethyl oxazoles and related thiazoles are described with samarium iodide. The convergent assembly of components 4 and 5 features formation of the fully substituted C22–C26 pyran by intramolecular capture of an allyl cation intermediate with high facial selectivity, and further efforts lead to E-C19/C20 olefination. The synthesis culminates with use of a modified Julia olefination for attachment of the C42–C46 segment and subsequent late-stage macrocyclization by installation of the (Z)-C2/C3 α,β-unsaturated lactone.
Related Links	http://dx.doi.org/10.1073/pnas.0402477101
Starting Page	12058
File Format	PDF
ISSN	10916490
e-ISSN	10916490
Journal	Proceedings of the National Academy of Sciences of the United States of America
Issue Number	33
Volume Number	101
Language	English
Publisher	National Academy of Sciences
Publisher Date	2004-08-17
Access Restriction	Open
Rights Holder	National Academy of Sciences
Subject Keyword	Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Multidisciplinary

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