Publication: Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions
Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions
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Iliev, B., Verma, S., Linden, A., & Heimgartner, H. (2006). Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions. Helvetica Chimica Acta, 89(2), 352–359. https://doi.org/10.1002/hlca.200690038
Abstract
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Abstract
The application of the ‘direct amide cyclization’ conditions to the linear delta-hydroxy diamide 11 is described (Scheme 3). Instead of the cyclization to the expected nine-membered cyclodepsipeptide, only the chloro acid 12 was obtained. Its formation could be explained by consecutive formation of the 1,3-oxazol-5(4H)-one 16 and the six-membered imino lactone 17 as intermediates (Scheme 4). The spontaneous isomerization of the latter gave 12 in a good yield.
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- Iliev, Boyan
- Verma, Sanjiv
- Heimgartner, Heinz
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Iliev, B., Verma, S., Linden, A., & Heimgartner, H. (2006). Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions. Helvetica Chimica Acta, 89(2), 352–359. https://doi.org/10.1002/hlca.200690038
