Tetronic acids and derivatives-IV

Pollet, P.; Gelin, Suzanne

doi:10.1016/0040-4020(78)80165-3

Cited by 30 publications

(14 citation statements)

References 17 publications

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“…Next we investigated the reactions of 5-monosubstituted 4-O-methyl tetronate 10. 17 Again 3-hydroxyalkylation products 12 were obtained in satisfactory to good yields (as ~1:1 mixtures of diastereomers) and with excellent regioselectivities ( Table 2, entries 6 and 7).…”

Section: Methodsmentioning

confidence: 94%

Highly Regioselective 3-Hydroxyalkylations of Boron 4-Methoxy-2-furanolates: A New Entry to 5-Unsubstituted and 5-Monosubstituted 3-Acyl-4-O-Methyl Tetronates

Paintner¹,

Allmendinger²,

Bauschke³

2001

Synthesis

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Section: Methodsmentioning

confidence: 94%

Highly Regioselective 3-Hydroxyalkylations of Boron 4-Methoxy-2-furanolates: A New Entry to 5-Unsubstituted and 5-Monosubstituted 3-Acyl-4-O-Methyl Tetronates

Paintner¹,

Allmendinger²,

Bauschke³

2001

Synthesis

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“…Clearly, a primary target had to be methyl tetronate (20) from which nucleophile (22) equivalent to species (23j(25), electrophile (26) equivalent to species such as (27), and radical (28) with precursors such as (29) could all be produced, as well as methyl 5-( 1'-methoxymethy1ene)tetronate (21). 3-Brom0-,~~, 3-rnethoxy~arbonyl-,~~ and 3-ethoxycarbonyltetronic acids 64 (30), (31), and (32) were prepared by pyrolysis of the corresponding 4-bromoacetoacetates.…”

Section: Rearrange Similarly To Butenolides (16) [Equation (3)]mentioning

confidence: 99%

“…84 "C/15 mmHg (8.75 g, 9473, was isolated by fractional distillation through an efficient Vigreux column. It must be kept under nitrogen and never exposed to moisture, and owing to its lability it was characterised by spectroscopy and by its reactions Tables 2 and 3. Methyl 5-bromotetronate (27). (i) Bromine (0.52 ml, 10 mmol) was added in one portion to a stirred solution of the lithium derivative (23) (10 mmol) (procedure B) at -78 "C. The mixture was allowed to warm to ca.…”

Section: B) Preparation Of Ethyl 4-bromo-3-methoxybut-2-enoate (34)mentioning

confidence: 99%

“…A better general method of introducing heteroatoms into the 5-position of compound (20) however is by low-temperature reaction of the 5-lithio derivative (23). Thus reaction of compound (23) with bromine gave a 97% yield of bromide (27), with diphenyl disulphide gave a 90% yield of methyl 5-(pheny1thio)tetronate (39, and with benzenesulphonyl chloride gave the 5-chloro derivative (36) in 92% yield. Oxidation of sulphide (35) with MCPBA gave methyl 5-(phenyl-sulphony1)tetronate (37) in 93% yield.…”

mentioning

confidence: 99%

“…Oxidation of sulphide (35) with MCPBA gave methyl 5-(phenyl-sulphony1)tetronate (37) in 93% yield. Although bromide (27) is not particuiarly stable, it required one week at room temperature in contact with water to yield methyl 5-hydroxytetronate (38) in 82% yield. Compound (38) has the trivial name of narthogenin and is the aglycone of the antibiotic n a r t h e ~i d e .…”

mentioning

confidence: 99%

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Synthetic routes to the piperolides, fadyenolides, epoxypiperolides, and related compounds

Pelter¹,

Al-Bayati²,

Ayoub³

et al. 1987

J. Chem. Soc., Perkin Trans. 1

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Syntheses of the piperolides, the fadyenolides, epoxypiperolide, and related compounds are described.( f ) -Narthogenin is also efficiently produced.From the Mexican plant Piper sanctum' we have previously isolated and characterised piperolide (l),' methylenedioxypiperolide (2),' ( + )-(7S,SS)-epoxypiperolide (3),'-" (-)-erythro-7,8-dihydro-7,8-dihydroxypiperolide (4),5 as well as a possible photoisomerisation product (5E)-piperolide (5),6*7 From Piper fudyenolii, indigenous to Jamaica, we have isolated and characterised similar butenolides, the fadyenolides (6) and (7).'These compounds are of particular interest for two reasons.First they are unique tetronates (derivatives of 4-hydroxybut-3-enolides) derived from higher plants rather than from fungal, microbial, or marine source^.^*^-'^ Secondly some of them, as well as certain of our synthetic products, have strong sedative as well as other most interesting physiological properties.It is tempting to speculate on a New World mutation in Piper species that leads from the usual pyrone derivatives such as kawain (8a)14 and methysticin (8b)14 produced by * We thank Dr. R. Pardasani for these experiments.

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Chiroptical properties, structure, and absolute configuration of heterosubstituted 2(5H)-furanones

Gawroński¹,

Chen²,

Geng³

et al. 1997

Chirality

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Chiroptical properties of a series of 3 and/or 4‐heterosubstituted 2(5H)‐furanones were investigated with respect to correlation with absolute configuration. The n − π* and π − π* Cotton effects have been assigned on the basis of comparison with the UV spectra in solvents of varying polarity. It is demonstrated that the n − π* transition in 4‐amino substituted 2(5H)‐furanones appears at shorter wavelength with respect to the π − π* transition. With the exception of 4‐pyrrolidino and 4‐benzylamino substituted 2(5H)‐furanones, other heterosubstituted 2(5H)‐furanones follow the butenolide configurational rule (Gawronski et al. J. Org. Chem. 61:1513–1515, 1996). Absolute configuration of 2(5H)‐furanone derivatives can also be assigned according to the sign of the Cotton effect (of unknown origin) at 200–230 nm. The structure of four representative sulfur and nitrogen substituted 2(5H)‐furanones has been analyzed by X‐ray diffraction. The results indicate planarity of the furanone ring and extended conjugation in 4‐amino substituted 2(5H)‐furanones. Chirality 9:537–544, 1997. © 1997 Wiley‐Liss, Inc.

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Tetronic acids and derivatives-IV

Cited by 30 publications

References 17 publications

Highly Regioselective 3-Hydroxyalkylations of Boron 4-Methoxy-2-furanolates: A New Entry to 5-Unsubstituted and 5-Monosubstituted 3-Acyl-4-O-Methyl Tetronates

Highly Regioselective 3-Hydroxyalkylations of Boron 4-Methoxy-2-furanolates: A New Entry to 5-Unsubstituted and 5-Monosubstituted 3-Acyl-4-O-Methyl Tetronates

Synthetic routes to the piperolides, fadyenolides, epoxypiperolides, and related compounds

Chiroptical properties, structure, and absolute configuration of heterosubstituted 2(5H)-furanones

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