An Unexpected Formation of a 14‐Membered Cyclodepsipeptide
Copyright policy )An Unexpected Formation of a 14‐Membered Cyclodepsipeptide
AbstractThe treatment of diluted solutions of the hydroxy diamides 6a and 6b in toluene with HCl gas at 100° gave the dimeric, 14‐membered cyclodepsipeptide 10 in up to 72% yield (Scheme 3). The same product was formed from the linear dimer of 6b, the depsipeptide 11, under the same conditions (cf. Scheme 4). All attempts to prepare the cyclic seven‐membered monomer 9, starting with different precursors and using different lactonization methods failed, and 10 was the only product which was isolated (cf. Scheme 6). For example, the reaction of the ester 20 with NaH in toluene at 80° led exclusively to the cyclodimer 10. On the other hand, the base‐catalyzed cyclization of the hydroxy diester 22, which is the ‘O‐analogue' of 20, yielded neither the seven‐membered dilactone, nor the 14‐membered tetralactone, but only the known trimer 23 and tetramer 24 of 2,2‐dimethylpropano‐3‐lactone (cf. Scheme 7).
- University of Zurich Switzerland
10120 Department of Chemistry, 1303 Biochemistry, 1503 Catalysis, 1604 Inorganic Chemistry, 3002 Drug Discovery, Organic Chemistry, Biochemistry, Catalysis, Inorganic Chemistry, 540 Chemistry, Drug Discovery, Physical and Theoretical Chemistry, 1606 Physical and Theoretical Chemistry, 1605 Organic Chemistry
10120 Department of Chemistry, 1303 Biochemistry, 1503 Catalysis, 1604 Inorganic Chemistry, 3002 Drug Discovery, Organic Chemistry, Biochemistry, Catalysis, Inorganic Chemistry, 540 Chemistry, Drug Discovery, Physical and Theoretical Chemistry, 1606 Physical and Theoretical Chemistry, 1605 Organic Chemistry
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