TY - JOUR
T1 - Enantioselective total syntheses of (-)-palau'Amine, (-)-axinellamines, and (-)-massadines
AU - Seiple, Ian B.
AU - Su, Shun
AU - Young, Ian S.
AU - Nakamura, Akifumi
AU - Yamaguchi, Junichiro
AU - Jørgensen, Lars
AU - Rodriguez, Rodrigo A.
AU - Ömalley, Daniel P.
AU - Gaich, Tanja
AU - Köck, Matthias
AU - Baran, Phil S.
PY - 2011/9/21
Y1 - 2011/9/21
N2 - Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'Amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels-Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments, are described.
AB - Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'Amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels-Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments, are described.
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U2 - 10.1021/ja2047232
DO - 10.1021/ja2047232
M3 - Article
C2 - 21861522
AN - SCOPUS:80052816929
VL - 133
SP - 14710
EP - 14726
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 37
ER -