Total synthesis of halipeptins: isolation of halipeptin D and synthesis of oxazoline halipeptin analogues |
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Authors: | Nicolaou K C Schlawe Daniel Kim David W Longbottom Deborah A de Noronha Rita G Lizos Dimitrios E Manam Rama Rao Faulkner D John |
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Institution: | Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA. |
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Abstract: | The isolation from the marine sponge Leiosella cf. arenifibrosa and structural elucidation of halipeptin D (5), a relative of the previously isolated halipeptins A-C (1-3), is described along with the total synthesis of a number of oxazoline analogues (7 a-d and epi-7 c-d). The developed synthetic strategy provides a flexible entry into the various isomers of the polyketide domain of the halipeptins and improvises for a late stage construction of the oxazoline ring after a macrolactamization process which secures the required macrocycle. |
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Keywords: | halipeptins natural products oxazolines peptides total synthesis |
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