The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C 16 –C 25  Fragment | Zendy

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

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The Reaction Mechanism of Spirocylization and Stereoselectivity Studies for the Calyculin C 16 –C 25 Fragment

Author(s) -

Rauhala Vesa,

Nättinen Kalle,

Rissanen Kari,

Koskinen Ari M. P.

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500206

Subject(s) - chemistry , intramolecular force , stereoselectivity , ring (chemistry) , stereochemistry , closure (psychology) , fragment (logic) , intramolecular reaction , catalysis , organic chemistry , computer science , economics , market economy , programming language

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 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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