Diacetone-glucose architecture as a chirality template. Part 9.1 Enantioselective synthesis of (R)-mevalonolactone and (R)-[2H9]mevalonolactone on carbohydrate template

Abstract

A highly enantioselective synthetic methodology for (R)-mevalonolactone has been developed based upon the chirality-transcription approach using a chiral template, diacetone-D-glucos-3-ulose 2. (R)-Mevalonolactone 1a is prepared from ketone 2 in 5 steps in 11% overall yield. This methodology is further applied to the synthesis of fully deuteriated (R)-[ 2 H 9 ]mevalonolactone 1b starting from ketone 2 and methyl [ 2 H 7 ]senecioate 7.

Anti-Food Allergic Compounds from Penicillium griseofulvum MCCC 3A00225, a Deep-Sea-Derived Fungus

“…By comparison of the NMR and MS data with those published in the literatures, 26 known compounds were determined to be aurantiomide C (11) [14], cyclopenin (12) [19], (−)-cyclopenol ( 13) [20], (3S)-1,4-benzodiazepine-2,5-diones ( 14) [21], 3-benzylidene-3,4dihydro-4-methyl-lH-l,4-benzodiazepine-2,5-dione ( 15) [22], 3-methyl-3,4-dihydroquinazo line-4-one ( 16) [23], 1,2-dihydro-2,3-dimethyl4(3H)quinazolinone ( 17) [24], N,N'-1,2-pheny lenebis-acetamide ( 18) [25], aconicarpyrazine B ( 19) [26], pyroglutamylleucinmethylester (20) 29) [32], methyl phydroxybenzeneacetate (30) [33], 2-hydroxy phenyl acetic acid (31) [34], methyl homogentisate (32) [35], 5-hydroxymethyl-furaldehyde (33) [36], leptosphaerone A (34) [37], 3-methyl-2-penten-5-olide (35) [38], and (R)-mevalonolactone (36) [39].…”

Multigram Synthesis of Mevalonolactone-d9 and Its Application to Stereochemical Analysis by 1H NMR of the Saturation Reaction in the Biosynthesis of the 2,3-Di-O-phytanyl-sn-glycerol Core of the Archaeal Membrane Lipid

“…We recently described the enantioselective synthesis of (R)-mevalonolactone-d 9 using chirality control on a carbohydrate template. 12 Since mavalonate kinases are generally highly enantioselective, 13 the deuterated probe could be a racemate for these biochemical studies. Therefore, a more convenient and easier synthesis was exploited for the preparation of such heavily deuterated molecules on a gram scale.…”

Chemical Constituents of the Deep-Sea-Derived Penicillium solitum

“…As a result, three new ( 1 – 3 ) and 22 known ( 4 – 25 ) compounds ( Figure 1 ) were obtained. By comparison of the NMR and MS data with those published in the literature, the known compounds were determined to be (−)-solitumidines D ( 4 ) [ 10 ], ML-236A ( 5 ) [ 13 ], solitumidine A ( 6 ) [ 10 ], methyl-2-([2-(1H-indol-3-yl)-ethyl]carbamoyl)acetate ( 7 ) [ 14 ], solitumine A ( 8 ) [ 10 ], indole-3-acetic acid methyl ester ( 9 ) [ 15 ], penicopeptide A ( 10 ) [ 16 ], (2′ S )-7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone ( 11 ) [ 17 ], hydroxypropan-2′,3′-diol orsellinate ( 12 ) [ 18 ], viridicatol ( 13 ) [ 19 ], viridicatin ( 14 ) [ 19 ], (−)-cyclopenol ( 15 ) [ 20 ], cyclopenin ( 16 ) [ 21 ], 3-benzylidene-3,4-dihydro-4-methyl-1 H -1,4-benzodiazepine-2,5-dione ( 17 ) [ 16 ], β -sitosterol-3- O - β - d -glucopyranoside ( 18 ) [ 22 ], cerebrosides C ( 19 ) [ 23 ], methyl-2,4-dihydroxy-3,5,6-trimethylbenzoate ( 20 ) [ 24 ], felinone A ( 21 ) [ 25 ], xylariphilone ( 22 ) [ 26 ], 5,6-dihydroxy-2,3,6-trimethylcyclohex-2-enone ( 23 ) [ 27 ], ( R )-mevalonolactone ( 24 ) [ 28 ], and 3-methyl-2-penten-5-olide ( 25 ) [ 29 ]. Here, we report the isolation, structure, and bioactivities of these 25 compounds.…”