Synthetic studies on chartelline C: Stereoselective construction of the core skeleton

Kotaro Iwasaki; Rentaro Kanno; Toshiharu Morimoto; Tohru Yamashita; Satoshi Yokoshima; Tohru Fukuyama

doi:10.1002/anie.201204726

Synthetic studies on chartelline C: Stereoselective construction of the core skeleton

Kotaro Iwasaki, Rentaro Kanno, Toshiharu Morimoto, Tohru Yamashita, Satoshi Yokoshima, Tohru Fukuyama

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert- butyldimethylsilyl.

Original language	English
Pages (from-to)	9160-9163
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	36
DOIs	https://doi.org/10.1002/anie.201204726
Publication status	Published - 2012 Sep 3

Keywords

Mitsunobu reaction
imidazole
natural products
spiro β-lactams
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201204726

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abstract = "What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert- butyldimethylsilyl.",

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AU - Iwasaki, Kotaro

AU - Kanno, Rentaro

AU - Morimoto, Toshiharu

AU - Yamashita, Tohru

AU - Yokoshima, Satoshi

AU - Fukuyama, Tohru

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Synthetic studies on chartelline C: Stereoselective construction of the core skeleton

Abstract

Keywords

ASJC Scopus subject areas

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