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Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide

โœ Scribed by Fumiaki Yokokawa; Takayuki Shioiri

Book ID
104252345
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
522 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The first total synthesis of somamide A (1), an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide, from the marine cyanobacterium Lyngbya majuscula is described. The efficient and stereospecific dehydration of the N-acyl threonine ester using Martin's sulfurane provided the (Z)-2-amino-2-butenoic acid residue. The macrolactamization using FDPP(Ph 2 P(O)OC 6 F 5 ), the final installation of the Ahp moiety by oxidation with 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide, and cyclization of the norvaline derivative to the cyclic hemiaminal afforded somamide A (1).

๐Ÿ“œ SIMILAR VOLUMES

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