Assignment of absolute configuration of 2-substituted-1-propanols by 1H NMR spectroscopy

Yasuhara, Fujiko; Yamaguchi, Shozo; Kasai, Ryoji; Tanaka, Osamu

doi:10.1016/s0040-4039(00)84903-5

Cited by 24 publications

(8 citation statements)

References 2 publications

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“…Since 1 and 2 both lack such a C-2 methyl group and display a consecutive chiral center, the method described by Tsuda does not seem relevant to establish their stereochemistry. However, these limitations do not stand longer with regard to the former publication of this strategy (Yasuhara et al, 1986) and further applications to various chemical scaffolds including MTPA esters of furan derivatives (Kubota et al, 2002), scalusamide (Tsuda et al, 2005), and cycloartanes (Wang et al, 2014) (see Fig. S1).…”

Section: Resultsmentioning

confidence: 99%

New erythritol derivatives from the fertile form of Roccella montagnei

Duong¹,

Huynh²,

Chavasiri

et al. 2017

Phytochemistry

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Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC value of 68.39 ± 3.46 μM.

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Section: Resultsmentioning

confidence: 99%

New erythritol derivatives from the fertile form of Roccella montagnei

Duong¹,

Huynh²,

Chavasiri

et al. 2017

Phytochemistry

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“…In some cases the minor isomer was not observed at all. The absolute configuration of 2-substituted-1-propanols can be assigned by the 1 H-NMR splitting patterns of the Mosher's ester [3]. Reverse phase HPLC was also used to distinguish between Mosher diastereoisomers.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Chiral Building Blocks for Use in Drug Discovery

Marino¹,

Stachurska-Buczek²,

Huggins³

et al. 2004

Molecules

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In the past decade there has been a significant growth in the sales of pharmaceutical drugs worldwide, but more importantly there has been a dramatic growth in the sales of single enantiomer drugs. The pharmaceutical industry has a rising demand for chiral intermediates and research reagents because of the continuing imperative to improve drug efficacy. This in turn impacts on researchers involved in preclinical discovery work. Besides traditional chiral pool and resolution of racemates as sources of chiral building blocks, many new synthetic methods including a great variety of catalytic reactions have been developed which facilitate the production of complex chiral drug candidates for clinical trials. The most ambitious technique is to synthesise homochiral compounds from non-chiral starting materials using chiral metal catalysts and related chemistry. Examples of the synthesis of chiral building blocks from achiral materials utilizing asymmetric hydrogenation and asymmetric epoxidation are presented.

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“…Yasuhara and co-workers reported that the signals for the C1 methylene protons in the 1 H NMR spectra for diastereoisomeric Mosher ester derivatives of chiral α-methyl substituted primary alcohols appear as characteristic multiplets. 18 For the (S,R)-diastereoisomer, the methylene protons each appear as a doublet of doublets while for the (S,S )-isomer, the same protons resonate as one doublet. This was in accord with the 1 H NMR spectra of the Mosher esters 18 and 19 derived from (R)-and (S )-16, respectively, as shown in Fig.…”

Section: Total Synthesis Of (؉)-Rottnestol (1)mentioning

confidence: 99%

Total synthesis of the marine sponge metabolites (+)-rottnestol, (+)-raspailol A and (+)-raspailol BTaken in part from the PhD thesis of I. R. Czuba, The University of Melbourne, 2002.

2003

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The asymmetric syntheses of (+)-rottnestol (1) and the related marine sponge metabolites (+)-raspailols A (5) and B (6) are described. The key step in each of these sequences was a Stille coupling to form the C9-C10 sp2-sp2 bond and connect the polyene sidechains to the appropriate optically active tetrahydropyran core. For rottnestol (1), both C12 epimers were synthesised by a coupling between stannane 7 and (R)- or (S)-8 followed by acid hydrolysis which allowed for the assignment of the absolute configuration at the remote C12 stereocentre as R upon comparison of chiroptical data of the synthetic material with that reported for the natural product. In accord with this, (12R)-raspailol A (5) was synthesised from stannane 7 and sidechain 9 and this compound also compared well with the data for natural material including sign and absolute value of the specific rotation. Finally, the same C12 epimer of raspailol B (6) was secured via a union between stannane 10 and iodide 9 and this also possessed a similar rotation to that described for the natural product. Thus, all three compounds appear to possess the (12R) configuration, while that of the core tetrahydropyran ring is the same as proposed originally.

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Assignment of absolute configuration of 2-substituted-1-propanols by 1H NMR spectroscopy

Cited by 24 publications

References 2 publications

New erythritol derivatives from the fertile form of Roccella montagnei

New erythritol derivatives from the fertile form of Roccella montagnei

Synthesis of Chiral Building Blocks for Use in Drug Discovery

Total synthesis of the marine sponge metabolites (+)-rottnestol, (+)-raspailol A and (+)-raspailol BTaken in part from the PhD thesis of I. R. Czuba, The University of Melbourne, 2002.

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