Synthesis Of Marine Alkaloids Research Articles

Synthesis of marine alkaloids leucettamines B and C by β-lactam ring rearrangement

ABSTRACTA new method for the synthesis of marine alkaloids leucettamines B and C from Leucetta sp. sponges is described. The key step is the base-promoted rearrangement of β-lactam into imidazolone ring. Leucettamines B and C as well as their N-benzoyl derivatives were obtained in high yields. Single-crystal structures of both leucettamines B and C were determined by X-ray diffraction confirming Z-configuration of double bond at 4-position of imidazolone.

Total Synthesis of (−)‐Nakadomarin A

AbstractA highly efficient 12‐step synthesis of the marine alkaloid (−)‐nakadomarin A has been accomplished. The key advanced intermediate, a tetracyclic ketone derivative, was constructed in just seven steps using a sequence that includes an asymmetric Pauson–Khand reaction, an Overman rearrangement reaction, a ring‐closing metathesis reaction, and an amination reaction. Late introduction of the furan ring during the synthesis of (−)‐nakadomarin A means that the key tetracyclic ketone derivative has the potential to serve as an advanced intermediate for the synthesis of related marine alkaloids.

Synthesis of manzacidin A and C: efficient construction of quaternary carbon stereocenters bearing nitrogen substituents

An efficient synthetic method for stereoselective construction of asymmetric quaternary carbon stereocenters, bearing nitrogen in the form of Boc-protected allyl amines, has been developed. This methodology is employed in the synthesis of marine alkaloids, manzacidin A and C.

ChemInform Abstract: Synthesis of Marine Alkaloids from the Oroidin Family

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Marine Alkaloids from the Oroidin Family

Oxidation with a difference: The complexity of the oroidin alkaloid family of marine natural products is generated biosynthetically from one simple alkene precursor, but has left the synthetic community with problems. The first total synthesis of the tetracyclic axinellamines (see structure) was recently completed. Key to the success was the chemoselective oxidative functionalization of imidazol(in)e rings (green).

Synthesis of Marine Alkaloid: 8,9‐Dihydrocoscinamide B and Its Analogues as Novel Class of Antileishmanial Agents.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of marine alkaloid: 8,9-Dihydrocoscinamide B and its analogues as Novel class of antileishmanial agents

A series of marine alkaloid 8,9-dihydrocoscinamide B, its analogues and indolylglyoxylamide derivatives have been synthesized and screened for their in vitro antileishmanial activity profile in promastigote and amastigote models. Compounds 7 and 10 have shown 99–100% inhibition against promastigotes and 97–98% inhibition against amastigotes at a concentration of 10 μg/ml.

An Efficient Synthesis of (1R,4S)-1-Methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine. A Formal Synthesis of (-)-Aphanorphine

We report a highly efficient synthesis of (1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine in six steps from 5. The present work constitutes a new formal synthesis of marine alkaloid (-)-aphanorphine.

Ortho-directed metallation of π-deficient heterocycles in connection with palladium-catalyzed biaryl cross-coupling — Synthesis of marine alkaloids of the pyridoacridine series

Connection between ortho-directed metallation of π-deficient heterocycles and Suzuki cross-coupling reactions provides a very efficient and fruitful strategy to polycyclic molecules of biological interest. The methodology is used to synthesize alkaloids or precursors and analogues of natural compounds of the pyrido[2,3,4-k,l]acridine series.Key words: marine alkaloids, pyrido[2,3,4-k,l]acridines, metallation, cross-coupling.

Ortho-directed metallation of π-deficient heterocycles in connection with palladium-catalyzed biaryl cross-coupling — Synthesis of marine alkaloids of the pyridoacridine series

Ortho-directed metallation of π-deficient heterocycles in connection with palladium-catalyzed biaryl cross-coupling — Synthesis of marine alkaloids of the pyridoacridine series

ChemInform Abstract: Enantioselective Total Synthesis of Marine Alkaloids, Manzamine A and Related Compounds

A review of our studies toward the enantioselective total synthesis of ircinal A, manzamine A and related compounds is presented in detail.