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Coupling reactions of 1-tributylstannyl-1-octen-3-ol catalyzed by palladium: The synthesis of PGB1 and coriolic acid

โœ Scribed by J.K. Stille; Mark P. Sweet

Book ID
104232913
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
285 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The palladium catalyzed coupling of (S)-E-1 -tributylstannyl-1 -octen-3-01 (3) with 2-(6 carbethoxyhexyl)-3-iodo-2-cyclopenten-I-one gave a 70% yield of the (S)-ethyl ester of PGBI. Coriolic acid was synthesized in 75% yield by coupling 3 with Z-lo-iododecenoic acid, demonstrating the tolerance of this coupling reaction to the carboxylic acid function.

The utilization of organotin reagents in place of other main group organometals in the transition metal catalyzed coupling reactions with organic electrophiles enjoys a number of distinct advantages, the most important of which are that the reaction takes place under mild, neutral

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