Synthesis of Marine Natural Products 1

Albizati, Kim F.; Martín, Vanessa; Agharahimi, M. R.; Stolze, D. A.

doi:10.1007/978-3-642-76835-4

Cited by 5 publications

(4 citation statements)

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“…Marine organisms are among the most promising sources of new biologically active molecules . Certain secondary metabolites are nontraditional guanidine-based alkaloids that possess a broad spectrum of powerful biological activities. The guanidine moiety is frequently found in the guise of a 2-aminoimidazole ring or a 2-aminopyrimidine ring, which represent an emerging structural class of marine alkaloids based upon their high degree of biological activity.…”

Section: Introductionmentioning

confidence: 99%

Carbodiimide-Mediated Preparation of the Tricyclic Pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidine Ring System and Its Application to the Synthesis of the Potent Antitumoral Marine Alkaloid Variolin B and Analog

2002

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A total synthesis of the marine alkaloid variolin B has been completed in 13 steps in an overall yield of 6.5% from 3-formyl-4-methoxypyridine. Our approach is based on the sequential formation of the 7-azaindole ring, the tricyclic pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine ring system, and finally installation of the 2-aminopyrimidine ring at C5. The required 7-azaindole ring appropriately substituted is formed by a modified indole synthesis involving a nitrene insertion process (two steps). Formation of the annelated pyrimidine ring is achieved by two routes both involving a carbodiimide-mediated cyclization process, which allow incorporation of the amine functionality at C9 of the core tricyclic (six steps). Installation of the northeast 2-aminopyrimidine ring at C5 is performed using the Bredereck protocol (three steps). Ultimate, thermal decarboxylation with concomitant O-methyl deprotection and further N-benzyl deprotection by the action of triflic acid completed the synthesis of the target natural product variolin B.

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Section: Introductionmentioning

confidence: 99%

Carbodiimide-Mediated Preparation of the Tricyclic Pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidine Ring System and Its Application to the Synthesis of the Potent Antitumoral Marine Alkaloid Variolin B and Analog

2002

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“…Marine organisms are among the most promising sources of new biologically active molecules. Certain secondary metabolites are nontraditional guanidine-based alkaloids that possess a broad spectrum of powerful biological activities. The guanidine moiety is most frequently found in the guise of a 2-aminoimidazole ring that embodies one or two benzyl-substituted moieties …”

mentioning

confidence: 99%

Synthesis of Marine Alkaloids Isonaamine A, Dorimidazole A, and Preclathridine A. Iminophosphorane-Mediated Preparation of 2-Amino-1,4-disubstituted Imidazoles from α-Azido Esters

1999

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“…Isolaurepinnacin ( 3 ) and trans -isoprelaurefucin ( 4 ) are examples of the rarer class of C 15 Laurencia acetogenins that contain seven-membered oxacyclic (oxepane) rings. Laurencia metabolites have been popular targets for synthetic investigations and have spurred the development of a number of new methods for constructing cyclic ethers …”

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confidence: 99%

Total Synthesis of (+)-Isolaurepinnacin. Use of Acetal-Alkene Cyclizations To Prepare Highly Functionalized Seven-Membered Cyclic Ethers

1997

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The first synthesis of the title compound is described. The synthesis features an acetal-vinylsilane cyclization to stereoselectively form the cis-2,7-disubstituted oxepene ring and introduce Δ4 unsaturation. Starting with (2R,3S)-2,3-epoxypentan-1-ol (16), mixed acetal 10 is formed in five steps and 72% overall yield. Treatment of 10 with excess BCl3 in CH2Cl2 at −78 → 0 °C promotes cyclization to afford Δ4-oxepene 39 in 90% yield after deprotection of the silyl ether. Elaboration of the (E)-enyne functionality of the six-carbon side chain completes the synthesis of (+)-isolaurepinnacin.

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Synthesis of Marine Natural Products 1

Cited by 5 publications

References 0 publications

Carbodiimide-Mediated Preparation of the Tricyclic Pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidine Ring System and Its Application to the Synthesis of the Potent Antitumoral Marine Alkaloid Variolin B and Analog

Carbodiimide-Mediated Preparation of the Tricyclic Pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidine Ring System and Its Application to the Synthesis of the Potent Antitumoral Marine Alkaloid Variolin B and Analog

Synthesis of Marine Alkaloids Isonaamine A, Dorimidazole A, and Preclathridine A. Iminophosphorane-Mediated Preparation of 2-Amino-1,4-disubstituted Imidazoles from α-Azido Esters

Total Synthesis of (+)-Isolaurepinnacin. Use of Acetal-Alkene Cyclizations To Prepare Highly Functionalized Seven-Membered Cyclic Ethers

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