The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C16–C25 Fragment

Vesa Rauhala, Kalle Nättinen (Corresponding Author), Kari Rissanen, Ari M.P. Koskinen (Corresponding Author)

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Abstract

The mechanism of the double intramolecular hetero‐Michael addition, a key reaction in the planned synthesis of the natural product calyculin C, has been studied by NMR. The cyclization follows Baldwin’s rules and proceeds first through a six‐membered ring closure (6‐endodig), followed by a five‐membered ring cyclization (5‐exotrig).
Original languageEnglish
Pages (from-to)4119-4126
JournalEuropean Journal of Organic Chemistry
Volume2005
Issue number19
DOIs
Publication statusPublished - 2005
MoE publication typeA1 Journal article-refereed

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Keywords

  • Michael addition
  • cyclization
  • NMR

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