Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species

Ueki, Toshihiko; Kinoshita, Takamasa

doi:10.1039/b407820a

Cited by 14 publications

(8 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is reported that butalactin exhibits moderate antibacterial activity against Gram-positive bacteria [4]. Based on this findings, some derivatives of g-butyrolactone (5-alkoxy-4-aminofuran-2(5H)-one) showing good antibacterial activity against multiresistant Staphylococcus aureus were reported [5].…”

Section: Discussionmentioning

confidence: 96%

Crystal structure of 3-(4-fluorophenyl)-4-hydroxyfuran-2(5H)-one, C10H7FO3

Xiao¹,

Zhu²,

Jiang³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

C 10 H 7 FO 3 ,monoclinic, P12 1 /c1(no. 14), a =7.584(2) Å, b =8.863(2) Å, c =12.707(3) Å, b =90.64(1)°, V =854.1 Å 3 , Z =4,R gt(F) =0.041, wRref(F 2 ) =0.107, T =296 K. Source of materialAs olution of 2-ethoxy-2-oxoethyl 2-(4-fluorophenyl)-acetate (0.96 g, 4mmol) in dry THF was added dropwise to asuspension of NaH in dry THF in an ice cold bath. The stirring was maintained at room temperature for 5h.Water was added and the solution was extracted twice with ethyl ether. The aqueous phase was cooled to 0°Cand then acidified with concentrated hydrochloric acid to give asolid precipitate. The title compound was crystallized from ethanol-water (2:1, v/v)t og ive the colorless blockshaped crystals suitable for single-crystal structure determination. DiscussionCompounds with g-butyrolactone-core (furanone) show diverse biological activities such as antitumor and anti-inflammatory activity [1][2][3]. It is reported that butalactin exhibits moderate antibacterial activity against Gram-positive bacteria [4]. Based on this findings, some derivatives of g-butyrolactone (5-alkoxy-4-aminofuran-2(5H)-one) showing good antibacterial activity against multiresistant Staphylococcus aureus were reported [5]. Recently, we focused our efforts to synthesize enamines with gbutyrolactone-core for antibacterial activity screening. In the title crystal structure, the bond length d(C7-C10) = 1.346(2) Å is in the range of atypical double bond (1.32 -1.38 Å), and the title compound was therefore identified as afuran-2(5H)-one not afuran-2(3H)-one. Because C9 attaches to adouble bond, s-p hyperconjugation occurring between C9-H9A (H9B) and C7-C10 slightly shortens C9-C10 bond from about 1.53 to 1.490(2) Å.C10-O3 (1.316(2) Å)bond length is shorter than the standard C-Osingle bond (1.41 -1.44 Å), but longer than C-O double bond (1.19 -1.23 Å). This clearly indicated that an sp 3 orbital of O3 is conjugated with the p molecular orbital of C7=C10 double bond, which was supported by the small torsion angle (-1.5(2)°)ofC1-C7-C10-O3. The stereochemistry of the double bond in lactone ring was assigned as (E)-configuration (figure, top). The butyrolactone moiety makes ad ihedral angle of 17.86(6)°with the 4-fluorophenyl group. In the title compound, the two independent hydrogen bonds generate at wo-dimensional layer of edge-fused centrosymmetric rings running parallel to (100), with R 2 2 (8) rings built from pairs of C-H···Fhydrogen bonds centred at (0,3n/2 +1,-1n/2), where n represents an integer, and with the R 6 6 (44) rings built from pairs of C-H···Fa nd O-H···Oh ydrogen bonds centred at (0,3n/2+1, 1n/2), where n again represents an integer (figure, bottom). The resulted layer has azigzag pattern in the cross section, running along the [010] direction. In al ayer, each R 6 6 (44) ring runs through by other two R 6 6 (44) rings which are from other two layers, respectively, and these layers (three) therefore interweave each other to form al ayered tablet. The title ompound extends further to its final three-dimensional network through ...

show abstract

Section: Discussionmentioning

confidence: 96%

Crystal structure of 3-(4-fluorophenyl)-4-hydroxyfuran-2(5H)-one, C10H7FO3

Xiao¹,

Zhu²,

Jiang³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

“…Both the fragments 4 and 6 are prepared separately according to known procedures and then combined in a later stage of the synthesis. Fragment 4 is prepared in eight steps and 53% overall yield starting from (S)-diethyl malate (2), according to known procedures (Scheme 2) [15,16]. Similarly, fragment 6 is prepared from (S)-propylene oxide (5) in three straightforward transformations giving the desired THP-protected, (S)-configured alkynol 6 in 58% overall yield [17].…”

Section: Enantioselective Total Synthesis Of Okaspirodiolmentioning

confidence: 99%

ChemInform Abstract: Asymmetric Synthesis of Naturally Occurring Spiroketals

Raju

Saikia

2009

ChemInform

View full text Add to dashboard Cite

show abstract

“…Both the fragments 4 and 6 are prepared separately according to known procedures and then combined in a later stage of the synthesis. Fragment 4 is prepared in eight steps and 53% overall yield starting from ( S )-diethyl malate ( 2 ), according to known procedures ( Scheme 2 ) [ 15 , 16 ]. Similarly, fragment 6 is prepared from ( S )-propylene oxide ( 5 ) in three straightforward transformations giving the desired THP-protected, ( S )-configured alkynol 6 in 58% overall yield [ 17 ].…”

Section: Asymmetric Total Synthesis Of Natural Spiroketalsmentioning

confidence: 99%