First Total Synthesis of (-)-Pericosine A from (-)-Shikimic Acid: Structure Revision and Determination of the Absolute Configuration of Antitumor Natural Product Pericosine A

Usami, Yoshihide; Horibe, Yusuke; Takaoka, Isao; Ichikawa, Hayato; Arimoto, Masao

doi:10.1055/s-2006-944197

Cited by 29 publications

(20 citation statements)

References 7 publications

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“…Structural motifs misassigned on the basis of NOEs include epoxides (calafianin, 96–98 symbiodinolide 99, 100 ), cyclopropyl rings (clavosolide A, 101, 102 laurentristich-4-ol 103, 104 ), bridges (vannusals A and B 105–107 ), fused ring junctions (itomanallene A, 108, 109 asperdimin, 110, 111 aplysiallene 112, 113 ), polyethers (aplysiol B, 114, 115 azaspiracids 116–119 ), vicinal polyols (amphidinolide H2, 120, 121 hyrtiosterol, 122, 123 pericosine A 124, 125 ), sugars (callipeltoside C; 126, 127 fusapyrone and deoxyfusapyrone, 128, 129 Table 6) and macrolides (palmerolide A, 130–132 neopeltolide 133, 134 ).…”

Section: Sources Of Natural Product Structural Misassignmentsmentioning

confidence: 99%

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Suyama

Gerwick

McPhail

2011

Bioorganic & Medicinal Chemistry

162

175

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The structural assignment of new natural product molecules supports research in a multitude of disciplines that may lead to new therapeutic agents and or new understanding of disease biology. However, reports of numerous structural revisions, even of recently elucidated natural products, inspired the present survey of techniques used in structural misassignments and subsequent revisions in the context of constitutional or configurational errors. Given the comparatively recent development of marine natural products chemistry, coincident with the modern spectroscopy, it is of interest to consider the relative roles of spectroscopy and chemical synthesis in the structure elucidation and revision of those marine natural products which were initially misassigned. Thus, a tabulated review of all marine natural product structural revisions from 2005 to 2010 is organized according to structural motif revised. Misassignments of constitution are more frequent than perhaps anticipated by reliance on HMBC and other advanced NMR experiments, especially considering the full complement of all natural products. However, these techniques also feature prominently in structural revisions, specifically of marine natural products. Nevertheless, as is the case for revision of relative and absolute configuration, total synthesis is a proven partner for marine, as well as terrestrial, natural products structure elucidation. It also becomes apparent that considerable ‘detective work’ remains in structure elucidation, in spite of the spectacular advances in spectroscopic techniques.

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Section: Sources Of Natural Product Structural Misassignmentsmentioning

confidence: 99%

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Suyama

Gerwick

McPhail

2011

Bioorganic & Medicinal Chemistry

162

175

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“…33.15) [129]. The stereochemistry of pericosine A was confirmed by its total synthesis from shikimic acid [130]. Pericosines A, B, and D inhibit the growth of murine P388 lymphocytic leukemia cells (ED 50 0.1, 4.0, 3.0 µg/mL, respectively) [131].…”

Section: Shikimate Derivativesmentioning

confidence: 88%

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Kigoshi

Kita

2014

Handbook of Anticancer Drugs From Marine Origin

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Sea hares (family Aplysiidae) are a rich source of bioactive substances. Especially, over the past 40 years, the genera Aplysia and Dolabella have afforded numerous bioactive secondary metabolites that exhibit antitumor activity. For example, the depsipeptide dolastatin 10 and its analogue are currently in cancer clinical trials. Meanwhile, the chemical probe approach has revealed that the antitumor macrolide aplyronine A inhibits microtubule assembly in association with actin. This article highlights the recent findings regarding the chemical biology of antitumor and antineoplastic compounds from sea hares, as well as molecules that have been discovered and characterized after 2000.Keywords Antitumor · Sea hare · Aplysia · Antitumor · Actin-deplymerization · Cytotoxicity · Tubulin IntroductionSea hares, which belong to the opisthobranch group of mollusks (clade Aplysiomorpha), are shell-less, slow-moving benthic marine mollusks [1]. The order Anaspidea includes two families, Akeridae and Aplysiidae [2]. Almost all chemical studies have focused on Aplysiidae specimens. The family Aplysiidae includes nine genera, Aplysia (Linnaeus 1767), Bursatella (Blainville 1817), Dolabella (Lamarck 1801), Dolabrifera (Gray 1847), Notarchus (Cuvier 1817), Petalifera (Gray 1847), Phyllaplysia (Fischer 1872), Syphonota (Adams 1854), and Stylocheilus (Gould 1852). Sea hares are herbivorous, and are typically found on seaweed in shallow water. They are not eaten by other marine animals and have been postulated to contain chemical defense substances. The poisonous properties of sea hare secretions were known in Roman times. In addition, sea hares release ink from their ink glands, which deter predators. This ink acts as a screen, while at the

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“…The first total synthesis of (À)-1 was achieved as shown in Scheme 4 [77,84]. Alcohol 15 derived from (À)-shikimic acid underwent Dess-Martin oxidation, affording b,g-unsaturated ketone 47.…”

Section: First Total Synthesis Of Revised Pericosine A: Determinationmentioning

confidence: 99%

“…Second-generation total syntheses of 1 and 3 were attempted in order to improve the overall yield as that of the first synthesis was unsatisfactory, that is, 0.57% from (À)-quinic acid [77,84]. During 1993 and 1994, two research SCHEME 6 Syntheses of pericosines D and D o .…”

Section: Second-generation Syntheses Of Pericosines a And C By The Usmentioning

confidence: 99%

Synthesis of Marine-Derived Carbasugar Pericosines

Usami

2014

Studies in Natural Products Chemistry

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First Total Synthesis of (-)-Pericosine A from (-)-Shikimic Acid: Structure Revision and Determination of the Absolute Configuration of Antitumor Natural Product Pericosine A

Cited by 29 publications

References 7 publications

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Synthesis of Marine-Derived Carbasugar Pericosines

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