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DOI: 10.1055/s-2003-38675
Applications of Size-Selective Macrolactonizations to the Synthesis of Benzolactone-Enamide Core Structures
Publication History
Publication Date:
16 April 2003 (online)
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Abstract
By utilizing Stille cross-coupling reactions four benzoic acid derivatives (18, 32, 46, 66) were prepared that carry a side chain with two secondary hydroxy groups. It could be shown that the hydroxy functions can be distinguished by size-selective macrolactonization reactions. Thus, 12-membered lactones 19 and 33 are favored over their 11-membered lactone counterparts 20 and 34, respectively, albeit with a low (60:40-70:30) ratio. The selectivity is much more pronounced if there is a competition between a 12- and 10-membered lactone. This could be shown with the two lactones 47 and 67. The 12-membered lactones 33, 47, and 67 represent core structures for analogs of the benzolactone enamides. The macrolactonization reactions were performed under Yamaguchi conditions.
Key words
alkynes - epoxides - hydrostannations - macrocycles - ring closure - Stille reaction
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