38634-44-5Relevant academic research and scientific papers
SYNTHESIS OF (+/-)-PYRENOPHORIN AND (+/-)-COLLETALLOL
Wakamatsu, Takeshi,Yamada, Satoshi,Ozaki, Yoshiko,Ban, Yoshio
, p. 1989 - 1992 (2007/10/02)
Pyrenephorin 1 and colletallol 3 were synthesized in their racemic forms from the corresponding hydrocarboxylic acids 9 and 14 via stereoselective formation of the requisite trans double bonds after macrocyclization.
NOVEL SYNTHETIC ROUTE γ-OXO-ACRYLATES Application to the synthesis of Pyrenophorin antibiotic
Dumont, W.,Vermeyen, C.,Krief, A.
, p. 2883 - 2886 (2007/10/02)
We report a new method for the synthesis of γ-oxo-acrylates which allows the direct introduction of suitably functionalised four carbon skeleton.
Enamines of 2,2-bis(ethylthio)ethanal: a convenient route to γ-keto crotonate derivatives
Bates, Gordon S.,Ramaswamy, S.
, p. 2466 - 2475 (2007/10/02)
A new α-oxoaldehyde reagent, 2,2-bis(ethylthio)ethanal 1, has been prepared in high yield from ethanedial.Alkylation of the potassium salt of the enamines of 1 with various alkylating agents followed by in situ hydrolysis of the intermediate imine afforded high yields of the alkylation products of 1.This new reagent was used in the synthesis of a chiral potential precursor of the macrocyclic fragment of cytochalasins A,B, and F, as well as in the syntheses of the physiologically active diolides pyrenophorin and norpyrenophorin.
A SHORT-STEP SYNTHESIS OF (+/-)-PYRENOPHORIN UTILIZING 3-ALKENOATE AS A MASKED SYNTHON OF 4-OXO-2-ALKENOATE
Fujisawa, Tamotsu,Takeuchi, Masashi,Sato, Toshio
, p. 1795 - 1798 (2007/10/02)
The use of 3-alkenoate as a masked synthon of 4-oxo-2-alkenoate was established by a three step conversion of 3-noneonate into 4-oxo-2-nonenoate through epoxidation, isomerization to an allyl silyl ether, and oxidation in a high overall yield.This method was applied to the short step synthesis of pyrenophorin from 7-oxo-3-octenoic acid.
A Short Synthesis of (R,R)-(-)-Pyrenophorin from (S)-Propylene Oxide and a 3-Pentenoic Acid d5-Reagent
Mali, Raghao S.,Pohmakotr, Manat,Weidmann, Beat,Seebach, Dieter
, p. 2272 - 2284 (2007/10/02)
Analysis of the known syntheses of pyrenophorin (1) (Scheme 1) reveals that they all rest upon the use of reagents with d1-, d3-, or a2-reactivity umpolung for the establishment of at least one of the 1,4-distances of functional groups.A different approach, outlined in Scheme 2, has now been realized: the non-conjugated and the conjugated 7-hydroxyoctenoic acids 10 and 11, obtained from dienone dianion derivatives of type 3 and d,l- or (S)-methyloxirane, are converted to the macrodiolides 12 and 13, respectively.These are directly oxidized with introduction of an oxygen function at position 4, see 13 -> 1 and 12 -> 16 -> 17 -> 1.The overall transformation of the γ,δ-unsaturated ketone 18 to pyrenophorin (1) in 27 percent yield takes six steps, partly without purification of intermediates.
SYNTHESIS OF (+/-)-PYRENOPHORIN UTILIZING 1,3-DIPOLAR CYCLOADDITION OF SILYL NITRONATE FOR THE CONSTRUCTION OF 16-MEMBERED RING
Asaoka, Morio,Mukuta, Takashi,Takei, Hisashi
, p. 735 - 738 (2007/10/02)
1-Methyl-4-nitrobutyl acrylate underwent 1,3-dipolar cycloaddition via its silyl nitronate to give isoxazoline derivative of 16-membered dilactone after acid treatment, from which (+/-)-pyrenophorin was synthesized.
The Reaction of 2-(Trialkylsiloxy)furans with Lead(IV) Acetate. The Synthesis of dl-Pyrenophorin
Asaoka, Morio,Yanagida, Noboru,Sugimura, Naoyuki,Takei, Hisashi
, p. 1061 - 1064 (2007/10/02)
The reaction of 2-(trimethylsiloxy)furans with lead(IV) acetate afforded the corresponding α,β-unsaturated γ-acetoxy-γ-lactones in good yields.The lactones were easily converted into the corresponding 3-acylacrylic acids.Utilizing this reaction, dl-pyrenophorin was synthesized.
