Total Synthesis of Palau'amine

Worth the wait: The long anticipated total synthesis of palau'amine has been accomplished by a route featuring highly chemoselective transformations, cascade reactions, and a remarkable transannular cyclization to secure the unprecedented trans‐5,5 ring junction (shown in red).

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Bibliographic Details
Published in:	Angewandte Chemie (International ed.) Vol. 49; no. 6; pp. 1095 - 1098
Main Authors:	Seiple, Ian B, Su, Shun, Young, Ian S, Lewis, Chad A, Yamaguchi, Junichiro, Baran, Phil S
Format:	Journal Article
Language:	English
Published:	Weinheim Wiley-VCH Verlag 01-02-2010 WILEY-VCH Verlag WILEY‐VCH Verlag
Subjects:	axinellamines Guanidines - chemical synthesis massadine Molecular Structure palau'amine Spiro Compounds - chemical synthesis total synthesis
Online Access:	Get full text
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Summary:	Worth the wait: The long anticipated total synthesis of palau'amine has been accomplished by a route featuring highly chemoselective transformations, cascade reactions, and a remarkable transannular cyclization to secure the unprecedented trans‐5,5 ring junction (shown in red).
Bibliography:	http://dx.doi.org/10.1002/anie.200907112 ark:/67375/WNG-9LZKG0MS-1 Amgen We are grateful to Lars Jørgensen and Dr. Tanja Gaich for technical assistance. We thank Prof. Dr. M. Köck for helpful discussions. Financial support for this work was provided by the NIH/NIGMS (GM-073949), Amgen, Bristol-Myers Squibb (postdoctoral fellowship to S.S.), the Japan Society for the Promotion of Science (JSPS) for a postdoctoral fellowship to J.Y., the Natural Sciences and Engineering Research Council of Canada (NSERC) for a postdoctoral fellowship to I.S.Y., the Canadian Institutes of Health Research (CIHR) for a postdoctoral fellowship to C.A.L., and the NSF for a predoctoral fellowship to I.B.S. ArticleID:ANIE200907112 NIH/NIGMS - No. GM-073949 istex:C67EB6029A1960395D0AF26805461CA49A569C6E We are grateful to Lars Jørgensen and Dr. Tanja Gaich for technical assistance. We thank Prof. Dr. M. Köck for helpful discussions. Financial support for this work was provided by the NIH/NIGMS (GM‐073949), Amgen, Bristol‐Myers Squibb (postdoctoral fellowship to S.S.), the Japan Society for the Promotion of Science (JSPS) for a postdoctoral fellowship to J.Y., the Natural Sciences and Engineering Research Council of Canada (NSERC) for a postdoctoral fellowship to I.S.Y., the Canadian Institutes of Health Research (CIHR) for a postdoctoral fellowship to C.A.L., and the NSF for a predoctoral fellowship to I.B.S. These authors contributed equally to this paper. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Both authors contributed equally to this paper.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200907112