Synthesis of the C-1027 Chromophore Framework through Atropselective Macrolactonization†
Masayuki Inoue Prof. Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Search for more papers by this authorTakeo Sasaki Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorSuguru Hatano
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorMasahiro Hirama Prof. Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorMasayuki Inoue Prof. Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Search for more papers by this authorTakeo Sasaki Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorSuguru Hatano
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorMasahiro Hirama Prof. Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Fax: (+81) 22-217-6566
Search for more papers by this authorThis work was supported by CREST, Japan Science and Technology Agency (JST). A fellowship to T.S. from the Japanese Society for the Promotion of Science (JSPS) is gratefully acknowledged.
Graphical Abstract
Weit reichende sterische Wechselwirkungen zwischen den 1,5-Diol-Schutzgruppen wurden bei der Synthese des Chromophorgerüsts von C-1027 für die erfolgreiche atropselektive Makrolactonisierung (A im Schema) genutzt. Darauf folgende LiN(SiMe3)2/CeCl3-unterstützte Acetylidaddition an eine Aldehydeinheit im System des starren Makrocyclus (B) lieferte das neungliedrige Zielringsystem mit einer hochgespannten Diineinheit.
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