Biological activities of IC201 ((3S,8E)-1,3-dihydroxy-8-decen-5-one), a low molecular weight immunomodulator produced by Streptomyces.

Mizutani, Shigetoshi; Odai, Hideharu; Masuda, Tohru; Iijima, Masatomi; Osono, Michiyo; Hamada, Masa; Naganawa, Hiroshi; Ishizuka, Masaaki; Takeuchi, Tomio

doi:10.7164/antibiotics.42.952

Cited by 19 publications

(12 citation statements)

References 8 publications

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“…[62] (+)-Streptenol A is a potent inhibitor of cholesterol biosynthesis with antitumor and immunostimulating activity. [63] In our synthesis the key intermediate 92 was synthesized starting from the dioxanone RAMP hydrazone (R)-37 through sequential a alkylation, auxiliary cleavage, and deoxygenation (Scheme 27). Removal of the TBS protecting group and TPAP-catalyzed oxidation afforded aldehyde 93, which was then transformed into (+)-streptenol A (94) in three further steps.…”

Section: The Samp/ramp-hydrazone Methodologymentioning

confidence: 99%

The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

2005

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Nature employs dihydroxyacetone phosphate (DHAP) as the donor component in various enzyme-catalyzed aldol reactions. Probably the most significant example in this regard is photosynthesis, in which D-glucose, the most widespread natural product, is formed in just a few steps from DHAP. In recent years a number of synthetic equivalents of DHAP have been reported that deserve particular attention, as their applicability in organic synthesis is not limited to (stereoselective) aldol reactions. The power of these reagents has also been demonstrated convincingly in numerous other asymmetric electrophilic alpha-substitution reactions in target-oriented syntheses. Furthermore, the related 1,3-dioxins are useful equivalents of 2-substituted acrolein derivatives.

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Section: The Samp/ramp-hydrazone Methodologymentioning

confidence: 99%

The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

2005

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“…[62] (+)-Streptenol A ist ein starker Inhibitor der Cholesterol-Biosynthese mit Antitumor-und immunstimulierender Aktivität. [63] Unsere Synthese beruhte auf der Herstellung des Schlüsselintermediats 92 durch sequenzielle aAlkylierung, Auxiliarspaltung und Desoxygenierung ausgehend von Dioxanon-RAMP-Hydrazon (R)-37 (Schema 27). Entfernen der TBS-Schutzgruppe und TPAP-katalysierte Oxidation führten zum Aldehyd 93, der in drei weiteren Stufen zu (+)-Streptenol A (94) umgesetzt wurde.…”

Section: Die Samp/ramp-hydrazonmethodeunclassified

Die Dihydroxyaceton‐Einheit – ein nützlicher C₃‐Baustein in der Organischen Synthese

2005

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Dihydroxyacetonphosphat (DHAP) dient der Natur als Methylenkomponente in verschiedensten enzymkatalysierten Aldolreaktionen. Das wohl wichtigste Beispiel in diesem Zusammenhang ist die Photosynthese, bei der d‐Glucose, der mengenmäßig bedeutendste Naturstoff, ausgehend von DHAP in nur wenigen Stufen gebildet wird. In den vergangenen Jahren wurde eine Vielzahl von synthetischen DHAP‐Äquivalenten entwickelt, die insofern besondere Aufmerksamkeit verdienen, als ihre Anwendbarkeit nicht auf (stereoselektive) Aldolreaktionen beschränkt ist. Die Reagentien stellten ihr Potenzial auch bei einer Reihe weiterer asymmetrischer elektrophiler α‐Substitutionen in zahlreichen zielgerichteten Synthesen überzeugend unter Beweis. Die verwandten 1,3‐Dioxine sind darüber hinaus nützliche Äquivalente 2‐substituierter Acroleine.

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“…The pheromone component 18, which was isolated from the olive fruit fly (Bactrocera oleae), 12 has been synthesized in seven steps via the reaction of 17 with 1 as a key step. 13 Similarly, starting from 19, the syntheses of Streptenol A (20) [14][15][16] and Streptenol B (21) 14 are now in progress and the details of these results will be reported in a full account.…”

Section: Resultsmentioning

confidence: 96%

Novel asymmetric oxy‐michael addition reaction of the chiral ketones to the achiral γ‐ or δ‐hydroxy‐α,β‐unsaturated carbonyl compounds

et al. 2001

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A novel asymmetric oxy-Michael addition reaction was developed. In the presence of a catalytic amount of base, chiral ketones 1 and 2, derived from D-glucose and D-fructose, respectively, reacted with omega-hydroxy enones or enoates 3a-e, 17 and 21 to form the hemiacetal-derived alkoxide which underwent stereoselective intramolecular Michael addition to give cyclic acetals. Although the stereoselectivities in the formation of the five-membered acetal rings were modest, six-membered ring formation proceeded with high stereoselectivity and the utility of the reaction was demonstrated by a simple syntheses of natural products.

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Biological activities of IC201 ((3S,8E)-1,3-dihydroxy-8-decen-5-one), a low molecular weight immunomodulator produced by Streptomyces.

Cited by 19 publications

References 8 publications

The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

Die Dihydroxyaceton‐Einheit – ein nützlicher C₃‐Baustein in der Organischen Synthese

Novel asymmetric oxy‐michael addition reaction of the chiral ketones to the achiral γ‐ or δ‐hydroxy‐α,β‐unsaturated carbonyl compounds

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Biological activities of IC201 ((3S,8E)-1,3-dihydroxy-8-decen-5-one), a low molecular weight immunomodulator produced by Streptomyces.

Cited by 19 publications

References 8 publications

The Dihydroxyacetone Unit—A Versatile C3Building Block in Organic Synthesis

The Dihydroxyacetone Unit—A Versatile C3Building Block in Organic Synthesis

Die Dihydroxyaceton‐Einheit – ein nützlicher C3‐Baustein in der Organischen Synthese

Novel asymmetric oxy‐michael addition reaction of the chiral ketones to the achiral γ‐ or δ‐hydroxy‐α,β‐unsaturated carbonyl compounds

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The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

The Dihydroxyacetone Unit—A Versatile C₃Building Block in Organic Synthesis

Die Dihydroxyaceton‐Einheit – ein nützlicher C₃‐Baustein in der Organischen Synthese