Absolute configuration of novel marine diterpenoid udoteatrial hydrate synthesis and cytotoxicities of ent-udoteatrial hydrate and its analogues

Ge, Yuting; Kondō, Shōichi; Katsumura, Shigeo; Nakatani, Kazuhiko; Isoe, Sachihiko

doi:10.1016/s0040-4020(01)81548-9

Cited by 15 publications

(3 citation statements)

References 21 publications

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“…via amino acids) to give iridoid alkaloids,16−18 a − presumably biomimetic − partial synthesis of gardenamide A ( 3 ) from its nitrogen‐free putative precursor genipine ( 1 ) seemed rewarding, also for a further proof of the absolute configuration of 3 . The absolute configuration of genipine ( 1 ) itself had previously been assigned in the course of a partial synthesis of the related natural product udoteatrial hydrate from 1 19…”

Section: Resultsmentioning

confidence: 99%

Gardenamide A fromRothmannia urcelliformis (Rubiaceae) − Isolation, Absolute Stereostructure, and Biomimetic Synthesis from Genipine

et al. 2001

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The iridoid alkaloid gardenamide A (3) was isolated from the phytochemically uninvestigated East African Rubiaceae species Rothmannia urcelliformis (Hiern) Bullock. Its absolute stereostructure was determined by quantum chemical CD calculations, which constitutes the first application of this useful chiroptical tool within the class of iridoids. An additional stereochemical proof succeeded by its biomimetic partial synthesis starting from the well‐known nitrogen‐free iridoid genipine (1).

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Section: Resultsmentioning

confidence: 99%

Gardenamide A fromRothmannia urcelliformis (Rubiaceae) − Isolation, Absolute Stereostructure, and Biomimetic Synthesis from Genipine

et al. 2001

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“…Synthesis of Methyl (1S,4aS,7aS)-1-(tert-Butyldimethylsilyloxy)-7hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate 31 (2) (Figure 1). To a stirred suspension of genipin (1.13 g, 5 mmol) and silver nitrate (2.12 g, 12.5 mmol) in dimethylformamide (DMF, 30 mL) was slowly added tert-butyldimethylsilyl chloride (1.88 g, 12.5 mmol) at 0 °C.…”

Section: ■ Introductionmentioning

confidence: 99%

Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents

Xia

Dong

et al. 2018

J. Agric. Food Chem.

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A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.

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“…The iridoids aucubin ( 19 ), catalpol, and asperuloside have previously been used synthetically as precursors of cyclopentanoids such as prostaglandins, − methyl jasmonate, and triquinanes . Also, the aglucone of geniposide ( 9 ), genipin, has been the starting material in semisyntheses of diterpenes from marine algae. − In addition, iridoid aglucones have been converted into pyridine monoterpene alkaloids and monoterpene piperidines . Although β-glucosidase is often used for sugar removal, simple acid-catalyzed hydrolysis of the glucoside bond or oxidative degradation of the sugar moiety may also be employed to obtain iridoid aglucones.…”

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confidence: 99%

Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

Franzyk¹,

Stermitz²

1999

J. Nat. Prod.

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Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29−34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

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Absolute configuration of novel marine diterpenoid udoteatrial hydrate synthesis and cytotoxicities of ent-udoteatrial hydrate and its analogues

Cited by 15 publications

References 21 publications

Gardenamide A fromRothmannia urcelliformis (Rubiaceae) − Isolation, Absolute Stereostructure, and Biomimetic Synthesis from Genipine

Gardenamide A fromRothmannia urcelliformis (Rubiaceae) − Isolation, Absolute Stereostructure, and Biomimetic Synthesis from Genipine

Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents

Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

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