Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Usami, Yoshihide; Hatsuno, Chikage; Yamamoto, Hiroe; Tanabe, Manabu; Numata, Atsushi

doi:10.1248/cpb.52.1130

Cited by 20 publications

(21 citation statements)

References 10 publications

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“…1 are structurally unique and highly functionalized C‐7 cyclohexenoid metabolites of Periconia byssoides OUPS‐N133, a fungus originally separated from the sea hare Aplysia kurodai 10, 11. The absolute configuration of pericosines A–D 1 , 2 , 3 , 4 had been elucidated by a series of synthetic studies 12–18. Pericosines A 1 , B 2 , and D 4 exhibit significant in vitro cytotoxicity to P388 murine cell lines.…”

Section: Introductionmentioning

confidence: 99%

Natural pericosines B and C as enantiomeric mixtures: Direct evidence by chiral HPLC analysis

2011

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Pericosines are carbasugar-type metabolites of Periconia byssoides OUPS-N133, a fungus that was originally separated from the sea hare Aplysia kurodai. It has been reported that pericosines C and E are enantiomeric mixtures. The difference in specific rotation between natural pericosine C and the synthetic one led to the conclusion that natural pericosine C is an enantiomeric mixture. Meanwhile, the small specific rotation of natural pericosine B compared to that of the synthetic one led to the deduction that natural pericosine B might also be an enantiomeric mixture. Then, racemic pericosines B and C were synthesized, and the direct enantioseparation of these racemic carbasugars was conducted with CHIRALPAK® IA and CHIRALPAK® AY-H, which are suitable columns for racemic pericosines B and C, respectively. Using chiral HPLC, we conclude that natural pericosines B and C exist as enantiomeric mixtures. A rare example of the application of direct chiral HPLC analysis to intact sugars or carbasugars was provided.

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Section: Introductionmentioning

confidence: 99%

Natural pericosines B and C as enantiomeric mixtures: Direct evidence by chiral HPLC analysis

2011

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“…As mentioned above, our early efforts toward the synthesis of pericosine B were not successful [73], so, as an alternative, we attempted the synthesis of the epimer of pericosine B (3) [75]. Synthesis of 3 is illustrated in Scheme 2.…”

Section: Synthesis Of Epimer Of Pericosine B: Synthesis Of (þ)-Pericomentioning

confidence: 99%

“…5 [79][80][81][82]95]. Interestingly 6 corresponds to the core section of the chlorine-containing natural product (75), which had previously been isolated from two kinds of fungi, and cyathiformine C (76), which are metabolites of basidiomycetous fungi [82,83,96,97].…”

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

“…However, nature sometimes provides interesting examples of natural products that exist as mixtures of enantiomers [102][103][104]. As mentioned in the introduction, pericosines C (3) and E (5) exist as enantiomeric mixtures [64,75], and the relative stereochemistry of 5 suggests that it is constructed by the connection of two monomeric pericosines (1 and 2) with opposite configurations. This means that the presence of the antipodes of monomeric 1 and 2 are possible in nature.…”

Section: Chiral Hplc Analyses Of Some Natural Pericosinesmentioning

confidence: 99%

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Synthesis of Marine-Derived Carbasugar Pericosines

Usami

2014

Studies in Natural Products Chemistry

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“…In a comprehensive review of data related to pericosines [54, 63, 64], close similarity between the 1 H-NMR coupling constants of natural pericosine A [54] and those of 7 [63] led us to deduce that the structure of natural pericosine A was 1 , as illustrated in Figure 3.…”

Section: Synthetic Efforts For Pericosinesmentioning

confidence: 99%

Synthetic Efforts for Stereo Structure Determination of Cytotoxic Marine Natural Product Pericosines as Metabolites of Periconia sp. from Sea Hare

Usami

Ichikawa

Arimoto

2008

IJMS

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Abstract:Pericosines are unique C 7 cyclohexenoid metabolites of Periconia byssoides OUPS-N133 fungus that was originally isolated from the sea hare, Aplysia kurodai. Pericosines show significant in vitro cytotoxicity against P388 lymphocytic leukemia cells. Pericosine A, in particular, shows the most potent activity and significant in vivo antitumor activity against P388 cells. Thus, pericosines are promising candidates for seed compounds of anticancer drugs. However, before the total syntheses of pericosines were accomplished, their stereo structures could not be determined by spectral analyses because they have multifunctionalized cyclohexenoid structures with torsional strain. In this review, synthetic efforts for pericosines in this decade are surveyed.

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Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Cited by 20 publications

References 10 publications

Natural pericosines B and C as enantiomeric mixtures: Direct evidence by chiral HPLC analysis

Natural pericosines B and C as enantiomeric mixtures: Direct evidence by chiral HPLC analysis

Synthesis of Marine-Derived Carbasugar Pericosines

Synthetic Efforts for Stereo Structure Determination of Cytotoxic Marine Natural Product Pericosines as Metabolites of Periconia sp. from Sea Hare

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