404936-52-3Relevant academic research and scientific papers
Applications of size-selective macrolactonizations to the synthesis of benzolactone-enamide core structures
Petri, Andreas F.,Kuehnert, Sven M.,Scheufler, Frank,Maier, Martin E.
, p. 940 - 955 (2007/10/03)
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.
Synthesis of the core structure of apicularen a by transannular cyclization.
Kuehnert, Sven M,Maier, Martin E
, p. 643 - 646 (2007/10/03)
[reaction: see text] An approach to the macrocyclic core of apicularen A is described. Thus, cross-coupling of the aryl triflate 7 with the vinylstannane 19 provided the styrene 20. Deprotection led to the dihydroxy acid 22. Through a size-selective macro
