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

Vesa Rauhala; Kalle Nättinen; Kari Rissanen; Ari M.P. Koskinen

doi:10.1002/ejoc.200500206

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

Vesa Rauhala
, Kalle Nättinen^*
, Kari Rissanen
, Ari M.P. Koskinen^*

^*Corresponding author for this work

VTT Technical Research Centre of Finland

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

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

Original language	English
Pages (from-to)	4119-4126
Journal	European Journal of Organic Chemistry
Volume	2005
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.200500206
Publication status	Published - 2005
MoE publication type	A1 Journal article-refereed

Keywords

Michael addition
cyclization
NMR

Access to Document

10.1002/ejoc.200500206

Cite this

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title = "The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C16–C25 Fragment",

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{\textquoteright}s rules and proceeds first through a six-membered ring closure (6-endo-dig), followed by a five-membered ring cyclization (5-exo-trig).",

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AU - Nättinen, Kalle

AU - Rissanen, Kari

AU - Koskinen, Ari M.P.

PY - 2005

Y1 - 2005

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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

M3 - Article

SN - 1434-193X

VL - 2005

SP - 4119

EP - 4126

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19