Diazonamide studies. A direct synthesis of the indole bis-oxazole fragment from tri- and tetra-peptides using biomimetic oxidative cyclizations

Sperry, Jonathan; Moody, Christopher J.

doi:10.1016/j.tet.2010.03.012

Cited by 18 publications

(9 citation statements)

References 41 publications

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“…148 In addition, two partial syntheses of diazonamides were also reported. 149,150 Zoanthamine alkaloids, as exemplied by the structures of zoanthamine 226, norzoanthamine 227, zoanthenol 228, and 28-deoxyzoanthenamine 229, are a small group of marine alkaloids originally isolated from colonial zoanthids of the genus Zoanthus sp. Aer completion of total syntheses of the alkaloids zoanthamine, norzoanthamine, and zoanthenol, 151 a detailed account on the solution of those synthetic challenges has been published.…”

Section: Alkaloids From Other Marine Organismsmentioning

confidence: 99%

Muscarine, imidaozle, oxazole and thiazole alkaloids

Jin

2013

Nat. Prod. Rep.

134

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Covering: July 2010 to June 2012. Previous review: Nat. Prod. Rep., 2011, 28, 1143-1191. Structurally diverse alkaloids containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, as well as their saturated congeners, are widely distributed in terrestrial and marine organisms and microorganisms. These naturally occurring secondary metabolites often exhibit extensive and pharmacologically important biological activities. The latest progress involving isolation, biological activities, chemical synthetic studies, and biosynthetic pathways of these natural products has been summarized in this review.

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Section: Alkaloids From Other Marine Organismsmentioning

confidence: 99%

Muscarine, imidaozle, oxazole and thiazole alkaloids

Jin

2013

Nat. Prod. Rep.

134

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“…[13] Dipeptide 18 obtained from racemic bromo-tryptophan 2b with N-Cbz-l-valine 9b was oxidized with DDQ to form the oxazole ring of 19. [14] Further peptidic coupling with N-sulfonyl-l-tyrosine 1c afforded key precursor 20.…”

Section: Introductionmentioning

confidence: 99%

Natural Products Originated from the Oxidative Coupling of Tyrosine and Tryptophan: Biosynthesis and Bioinspired Synthesis

Tang

Vincent

2020

Chemistry A European J

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The oxidative coupling of tyrosine and tryptophan units is a pivotal step in the total synthesis of some peptide‐derived marine and terrestrial natural products, such as the diazonamides, azonazine and tryptorubin A. This Minireview details the biosynthesis and bioinspired synthesis of natural products with such structures. A special focus is put on the challenges of the synthesis of these natural products and the innovative solutions adopted by synthetic chemists.

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“…The3 -linked o-phenolic 3H-indole in that case exists as its aminal tautomer;g iving ac ore motif that was unknown at the time it was first described in diazonamides. [5][6][7] Assembling the core of the molecule was ap articular challenge. [5][6][7] Assembling the core of the molecule was ap articular challenge.…”

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confidence: 99%

“…[4] Structure 1 drew intense interest from the synthetic community and methods were forged to prepare the natural product. [7,8] Among solutions to the problem, ours was an attempt to parallel biosynthesis.W ef ound that PhI(OAc) 2 would mediate the conversion of peptidyl derivative 2 ( Figure 2, R = o-NO 2 PhSO 2 )t oi someric aminals 3a and 4a. [7,8] Among solutions to the problem, ours was an attempt to parallel biosynthesis.W ef ound that PhI(OAc) 2 would mediate the conversion of peptidyl derivative 2 ( Figure 2, R = o-NO 2 PhSO 2 )t oi someric aminals 3a and 4a.…”

mentioning

confidence: 99%

“…[4] Structure 1 drew intense interest from the synthetic community and methods were forged to prepare the natural product. [5][6][7] Assembling the core of the molecule was ap articular challenge. [7,8] Among solutions to the problem, ours was an attempt to parallel biosynthesis.W ef ound that PhI(OAc) 2 would mediate the conversion of peptidyl derivative 2 (Figure 2, R = o-NO 2 PhSO 2 )t oi someric aminals 3a and 4a.…”

mentioning

confidence: 99%

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Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide‐Based Drug Development Candidate

Ding,

DeRoy,

Perreault

et al. 2015

Angewandte Chemie

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An electrochemical method to synthesize the core macrolactam of diazonamides is described. Large ring-forming dehydrogenation is initiated by anodic oxidation at ag raphite surface.T he reaction requires no tailoring of the substrate and occurs at ambient temperature in aqueous DMF in an undivided cell open to air.T his unique chemistry has enabled aconcise,scalable preparation of DZ-2384;arefined analog of diazonamideAs lated for clinical development as ac ancer therapeutic.

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Diazonamide studies. A direct synthesis of the indole bis-oxazole fragment from tri- and tetra-peptides using biomimetic oxidative cyclizations

Cited by 18 publications

References 41 publications

Muscarine, imidaozle, oxazole and thiazole alkaloids

Muscarine, imidaozle, oxazole and thiazole alkaloids

Natural Products Originated from the Oxidative Coupling of Tyrosine and Tryptophan: Biosynthesis and Bioinspired Synthesis

Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide‐Based Drug Development Candidate

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