Synthesis of the Racemate and Both Enantiomers of Massoilactone

Ishikawa, Masashi; Amaike, Masayasu; Itoh, Masamichi; Warita, Yasuhiro; Kitahara, Takeshi

doi:10.1271/bbb.67.2210

Cited by 14 publications

(6 citation statements)

References 31 publications

(20 reference statements)

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“…2. The structures of massoia lactones were unambiguously ascertained by NMR (Table 3), the chemicals shifts and coupling constants were in agreement with the literature [14,23].…”

Section: Separation Of Massoia Lactones By Preparative Hydrostatic CCCsupporting

confidence: 80%

Hydrostatic countercurrent chromatography and ultra high pressure LC: Two fast complementary separation methods for the preparative isolation and the analysis of the fragrant massoia lactones

Urbain¹,

Corbeiller²,

Aligiannis³

et al. 2010

J of Separation Science

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Using a one-step preparative hydrostatic countercurrent chromatography method, the fragrant massoia lactones were purified from the crude massoia bark oil, in less than 3 h. The fractionation was performed with the biphasic solvent system c-hexane-methanol-water (10:9:1, v/v/v), leading to target compounds with purity over 96%, as determined by GC-MS and ultra high pressure LC-MS analyses. Together with C-10, C-12 and C-14 massoia lactones, two other aromatic compounds used in perfumes, benzyl benzoate and benzyl salicylate, were also obtained as pure compounds. In parallel, an easy and efficient ultra high pressure LC method was developed for the ultra-fast analysis of massoia lactones, as an alternative to long GC-MS methods.

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“…2. The structures of massoia lactones were unambiguously ascertained by NMR (Table 3), the chemicals shifts and coupling constants were in agreement with the literature [14,23].…”

Section: Separation Of Massoia Lactones By Preparative Hydrostatic CCCsupporting

confidence: 80%

Hydrostatic countercurrent chromatography and ultra high pressure LC: Two fast complementary separation methods for the preparative isolation and the analysis of the fragrant massoia lactones

Urbain¹,

Corbeiller²,

Aligiannis³

et al. 2010

J of Separation Science

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“…Fucosyl donor 4 was synthesized from tetra- O -acetyl- d -fucopyranose through two steps with an overall yield of 77% following the procedure reported in literature. ( S )-4-Hydroxy-1-nonene ( 5a ) and ( R )-4-hydroxy-1-nonene ( 5b ) were synthesized from ( S )-(+)-epichlorohydrin and ( R )-(−)-epichlorohydrin through three steps with overall yields of 68% and 58%, respectively.…”

Section: Experimental Sectionmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Ipomoeassin F and Its Unnatural 11R-Epimer

et al. 2015

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Ipomoeassin F, a macrolide glycoresin containing an embedded disaccharide, possesses potent in vitro antitumor activity with an unknown mechanism of function. It inhibits tumor cell growth with single-digit nanomolar IC50 values, superior to many clinical chemotherapeutic drugs. To facilitate translation of its bioactivity into protein function for drug development, we report here a new synthesis for the gram-scale production of ipomoeassin F (3.8% over 17 linear steps) from commercially-available starting materials. The conformation-controlled subtle reactivity differences of the hydroxyl groups in carbohydrates were utilized to quickly construct the disaccharide core, which, along with judicial selection of protecting groups, made the current synthesis very efficient. The same strategy was also applied to the smooth preparation of the 11R-epimer of ipomoeassin F for the first time. Cytotoxicity assays demonstrated the crucial role of the natural 11S configuration. In addition, cell cycle analyses and apoptosis assays on ipomoeassin F and/or its epimer were conducted. This work has laid a solid ground for understanding the medicinal potential of the ipomoeassin family of glycolipids in the future.

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“…First we selected n-hexanal (3) as a C-6 aldehyde and (S)-BINOL-Ti(OPr i ) 4 as a chiral complex, and explored the enantioselective aldol-type reaction of diketene (2). This reaction of 2 with 3 gave optically active 5-hydroxy-3oxodecanoate (6).…”

Section: Resultsmentioning

confidence: 99%

“…The obtained 1 was completely identical with authentic 1 in IR, MS and NMR spectral properties. 2 The optical purity value for 1 was shown to be 43% ee by a GLC analysis, using a chiral GLC column with cyclodextrin derivatives (Scheme 1). 7 We thought aromatic aldehyde had binding force with the complexes, but that of n-hexanal was weak.…”

Section: Resultsmentioning

confidence: 99%

“…1,2 The absolute configuration of natural 1 was determined to be (R)-form by the synthesis of unnatural (S)-isomer, and many reports on the various asymmetric syntheses of 1 have been published. 2,3 Since 1 is very useful as a butter and milk flavour but not widely available due to the limited cutting of massoia, many efforts have been devoted to its synthesis.…”

Section: Introductionmentioning

confidence: 99%

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