Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.

Odriozola, José M.; Garcı́a, Jesús M.; González, Anaisa Hernández; Gil, Pilar

doi:10.1016/s0957-4166(99)00528-5

Cited by 10 publications

(5 citation statements)

References 12 publications

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“…Acetylation of the hydroxyl group was followed by an ozonolysis with a reductive workup to give the primary alcohols 9b and 9c . Finally, tosylation and global reduction completed the synthesis of cruentol 10b and ferrugineol , 10c (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

et al. 2014

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A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.

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Section: Results and Discussionmentioning

confidence: 99%

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

et al. 2014

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“…Therefore, we sought in the literature the diastereomers of an isolated 1-hydroxy-2-methyl moiety whose 13 C NMR data were reported. We found that diasteromers of cruentol (5-methyloctan-4-ol) and ferrugineol (4-methylnonan-5-ol) were suitable for comparison of the NMR data with those of 9 . − Although the 13 C NMR data of these compounds were reported in CDCl 3 without assignments, it was possible to single out the chemical shift values of the branched methyl group. The chemical shifts of the relevant carbon were not identical for the ( R *, R *)- (or threo -) and ( S *, R *)- (or erythro -) isomers in both compounds (δ C 13.6 for the threo -isomer and δ C 15.2 for the erythro -isomers), implying that the branched methyl in the threo -isomers is more shielded than that in the erythro -isomers.…”

Section: Resultsmentioning

confidence: 99%

Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge Theonella swinhoei

et al. 2016

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Yakushinamides A (1) and B (2), prolyl amides of polyoxygenated fatty acids, have been isolated from the marine sponge Theonella swinhoei as inhibitors of HDACs and SIRTs. Their planar structures were determined by interpretation of the NMR data of the intact molecules and tandem FABMS data of the methanolysis products. For the assignment of the relative configurations of the three contiguous oxymethine carbons in 1 and 2, Kishi's universal NMR database was applied to the methanolysis products. During the assignments of relative configurations of the isolated 1-hydroxy-3-methyl moiety in 1 and the isolated 1-hydroxy-2-methyl moiety in 2, we found diagnostic NMR features to distinguish each pair of diastereomers. The absolute configurations of 1 and 2 were determined by a combination of the modified Mosher's method and Marfey's method. Although the modified Mosher's method was successfully applied to the methanolysis product of 1, this method gave an ambiguous result at C-20 when applied to the methanolysis product of 2, even after oxidative cleavage of the C-14 and C-15 bond.

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“…86,209 Furthermore, a-methyl secondary alcohols (44)(45)(46) were synthesized by asymmetric aldol condensation using an imide of another chiral oxazolidinone (R-1-4e). 137 The boron enolate derivative from the imide was treated with n-pentanal or n-butanal to afford syn adducts. Cleavage of the chrial auxiliary by LiBH 4 produced C 7 and C 6 1,3diols with a methyl group at the same 2-position, which were converted to pheromones with an S,S conguration.…”

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

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Insect pheromones are some of the most interesting natural products because they are utilized for interspecific communication between various insects, such as beetles, moths, ants, and cockroaches. A large number of compounds of many kinds have been identified as pheromone components, reflecting the diversity of insect species. While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques. Furthermore, their stereoselective syntheses have been achieved by employing trustworthy chiral sources and ingenious enantioselective reactions. The information has been reviewed here not only to make them available for new research but also to understand the characteristic chemical structures of the chiral pheromones. Since biosynthetic studies are still limited, it might be meaningful to examine whether the structures, particularly the positions and configurations of the branched methyl groups, are correlated with the taxonomy of the pheromone producers and also with the function of the pheromones in communication systems.

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Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.

Cited by 10 publications

References 12 publications

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge Theonella swinhoei

Chiral methyl-branched pheromones

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Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.

Cited by 10 publications

References 12 publications

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C2-Symmetrical Terminal Bis-Epoxide

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C2-Symmetrical Terminal Bis-Epoxide

Yakushinamides, Polyoxygenated Fatty Acid Amides That Inhibit HDACs and SIRTs, from the Marine Sponge Theonella swinhoei

Chiral methyl-branched pheromones

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A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide