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)

Research output: Contribution to journalArticleScientificpeer-review

22 Citations (Scopus)

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

Fingerprint

Stereoselectivity
Cyclization
fragments
rings
Biological Products
closures
Nuclear magnetic resonance
nuclear magnetic resonance
synthesis
products
calyculin C

Keywords

  • Michael addition
  • cyclization
  • NMR

Cite this

Rauhala, Vesa ; Nättinen, Kalle ; Rissanen, Kari ; Koskinen, Ari M.P. / The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C16–C25 Fragment. In: European Journal of Organic Chemistry. 2005 ; Vol. 2005, No. 19. pp. 4119-4126.
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The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C16–C25 Fragment. / Rauhala, Vesa; Nättinen, Kalle (Corresponding Author); Rissanen, Kari; Koskinen, Ari M.P. (Corresponding Author).

In: European Journal of Organic Chemistry, Vol. 2005, No. 19, 2005, p. 4119-4126.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C16–C25 Fragment

AU - Rauhala, Vesa

AU - Nättinen, Kalle

AU - Rissanen, Kari

AU - Koskinen, Ari M.P.

PY - 2005

Y1 - 2005

N2 - 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‐endo‐dig), followed by a five‐membered ring cyclization (5‐exo‐trig).

AB - 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‐endo‐dig), followed by a five‐membered ring cyclization (5‐exo‐trig).

KW - Michael addition

KW - cyclization

KW - NMR

U2 - 10.1002/ejoc.200500206

DO - 10.1002/ejoc.200500206

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 19

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