Stereoselective synthesis of pinnamine, an alkaloidal marine toxin from Pinna muricata

Kigoshi, Hideo; Hayashi, Niichi; Uemura, Daisuke

doi:10.1016/s0040-4039(01)01583-0

Cited by 33 publications

(24 citation statements)

References 6 publications

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“…Acid treatment resulted in cyclization and concomitant epimerization to the Cbz-protected pinnamine 505. 138 Alkylation of the magnesium bromide salt of ketimine 506 with the tosylate 507 in THF afforded, after acid hydrolysis, the keto olefin 508 (Scheme 93). 139 The latter is the key intermediate in the synthesis of R-multistriatin (510), a component of the aggregation pheromone of the European elm bark beetle, Scolytus multistriatus.…”

Section: Synthesis Of O-containing Bicyclic and Polycyclic Compoundsmentioning

confidence: 99%

1-Azaallylic Anions in Heterocyclic Chemistry

2004

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Section: Synthesis Of O-containing Bicyclic and Polycyclic Compoundsmentioning

confidence: 99%

1-Azaallylic Anions in Heterocyclic Chemistry

2004

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“…The structure and absolute configuration of pinnamine 3 were determined by a combination of spectroscopic means and asymmetric synthesis [22,23]. …”

Section: Introductionmentioning

confidence: 99%

The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors

Wonnacott

Gallagher

2006

Marine Drugs

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“…13) [47–50]. The absolute stereochemistry of 20 was also supported by a synthetic study [51]. Pinnamine exhibited significant acute toxicity against mice, with an LD 99 of 0.5 mg/kg.…”

Section: Resultsmentioning

confidence: 93%

Bioactive Alkaloids from the Sea: A Review

2004

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In our ongoing search for bioactive substances from marine organisms, novel alkaloids have been isolated. Pinnatoxins and pinnamine, potent shellfish poisons, were purified from the Okinawan bivalve Pinna muricata. Pinnatoxins activate Ca 2+ channels. Halichlorine was isolated from the marine spongeHalichondria okadai. This compound inhibits the induction of VCAM-1. Drugs that block VCAM-1 may be useful for treating coronary artery diseases, angina, and noncardiovascular inflammatory diseases. Pinnaic acids, which are cPLA 2 inhibitors, were also obtained from P. muricata. Interestingly, the structures of pinnaic acids are closely related to that of halichlorine. Norzoanthamine hydrochloride, isolated from the colonial zoanthid Zoanthus sp., suppresses decreases in bone weight and strength in ovariectomized mice, and could be a good candidate for an osteoporotic drug. Ircinamine, purified from the marine sponge Ircinia sp., has a reactive thioester. Aburatubolactams, inhibitors of superoxide anion generation, were isolated from Streptomyces sp. This article covers the bioactive marine alkaloids that have been recently isolated by this research group.

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Stereoselective synthesis of pinnamine, an alkaloidal marine toxin from Pinna muricata

Cited by 33 publications

References 6 publications

1-Azaallylic Anions in Heterocyclic Chemistry

1-Azaallylic Anions in Heterocyclic Chemistry

The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors

Bioactive Alkaloids from the Sea: A Review

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