2009
DOI: 10.1515/znb-2009-0615
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Synthesis of a Regular 24-membered Cyclodepsipeptide by Direct Amide Cyclization

Abstract: The synthesis of a 24-membered cyclic depsipeptide with an alternating sequence of phenyllactic acid and α-aminoisobutyric acid (Aib) is described. The linear precursor was prepared via the 'azirine/oxazolone method' using 2,2-dimethyl-3-amino-2H-azirines as building blocks for the α,α-disubstituted α-amino acid Aib. The macrolactonization leading to the cyclodepsipeptide was achieved by the 'direct amide cyclization', i. e., by treatment of a solution of the linear precursor in toluene with HCl gas.

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Cited by 6 publications
(4 citation statements)
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“…The structure of the latter has been established by X-ray crystallography as the 18-membered (R,S,S)-isomer (4a) (Kö ttgen et al, 2006). Similar results were obtained with analogous hexadepsipeptides (Kö ttgen et al, 2006), as well as with a homologue of (3a) to give the corresponding 24-membered cyclodepsipeptide (Kö ttgen et al, 2009). Unexpectedly, both (4a) and the 24-membered homologue were formed stereoselectively as epimers of the expected products.…”
Section: Introductionsupporting
confidence: 62%
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“…The structure of the latter has been established by X-ray crystallography as the 18-membered (R,S,S)-isomer (4a) (Kö ttgen et al, 2006). Similar results were obtained with analogous hexadepsipeptides (Kö ttgen et al, 2006), as well as with a homologue of (3a) to give the corresponding 24-membered cyclodepsipeptide (Kö ttgen et al, 2009). Unexpectedly, both (4a) and the 24-membered homologue were formed stereoselectively as epimers of the expected products.…”
Section: Introductionsupporting
confidence: 62%
“…In an analogous manner, the tetradepsipeptide amide (5a) was synthesized using 3-dimethylamino-2,2-dimethyl-2H-azirine, i.e. (1a), as the synthon for 2-aminoisobutyric acid (Aib) (Obrecht & Heimgartner, 1990;Kö ttgen et al, 2009). Similarly, reaction of racemic mandelic acid [Mns,(2b), 3.16 g] with an equimolar amount of (1b) (2.87 g) in 120 ml of acetonitrile after 1.5 h at room temperature gave the diamide (6) (R = Ph, 5.55 g) in 92% yield (Magirius, 1995).…”
Section: Synthesis and Crystallizationmentioning
confidence: 99%
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“…Oxazalones exhibited promising photo physical and photochemical activities [19], so they are used in semiconductor devices such as electro photographic photoreceptors and in non-linear optical materials [20]. Oxazalones has cyclooxygenase-2 inhibitory property [21] and tyrosine's inhibitory property.…”
Section: Introductionmentioning
confidence: 99%