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Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics

✍ Scribed by Anthony D Piscopio; John F Miller; Kevin Koch


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
573 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis


Complimentary solid phase syntheses of the Freidinger lactam class of 13-turn mimetics have been developed using ring closing metathesis as both the key carbon-carbon bond forming step and the cyclative cleavage mechanism. Solid phase variants of the Fukuyarna-Mitsunobu proce/ss were utilized as part of a rapid three-step sequence to construct immobilized lactarn precursors. An alternative solid phase process is offered which utilizes an Ugi/ring closing metathesis reaction tandem to deliver the desired compounds in two synthetic operations.