Formal synthesis of (−)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality

Cordero-Rivera, Reyna E.; Meléndez-Rodrı́guez, Myriam; Suárez‐Castillo, Oscar R.; Bautista-Hernández, Claudia I.; Trejo‐Carbajal, Nayely; Cruz-Borbolla, Julián; Castelán-Duarte, Luis E.; Morales‐Ríos, Martha S.; Joseph‐Nathan, Pedro

doi:10.1016/j.tetasy.2015.05.009

Cited by 13 publications

(4 citation statements)

References 45 publications

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“…Levorotatory flustramine B, occurring in the bryozoa Flustra foliacea (L.), was synthesized and its AC was determined by VCD and VCDEC as (3a S ,8a R )-( 273 ) (Figure 78) through the AC of oxazolidinone and amide intermediates. 130 Similar studies of indolyl derivatives were developed for the AC assignment of secondary alcohols in the ester series 131 and primary amines in the amide series. 132…”

Section: Resultsmentioning

confidence: 93%

“…Exceptions to such calculations are those limited cases for which VCDEC was employed. 33,40,73,74,88,91,112,130 -132 A relevant aspect of the calculation task is the selection of the level of theory that has to be used to provide a good spectra comparison and consequently a confident AC assignment, which implies balancing spectra similarity and invested computer resources for the calculations. This situation is not very relevant when a single stereogenic center is present in the molecule under study since the AC is correctly defined in most cases, although with different levels of confidence.…”

Section: Resultsmentioning

confidence: 99%

“…128 Reactions of glutaraldehyde with the 4 stereoisomers of commercial sphingosine generated the respective tricyclic products 269-272 ( Figure 77 129 Levorotatory flustramine B, occurring in the bryozoa Flustra foliacea (L.), was synthesized and its AC was determined by VCD and VCDEC as (3aS,8aR)-(273) (Figure 78) through the AC of oxazolidinone and amide intermediates. 130 Similar studies of indolyl derivatives were developed for the AC assignment of secondary alcohols in the ester series 131 and primary amines in the amide series. 132 The AC of a levorotatory alkaloid, found in Galanthus woronowii and G. nivalis, was established using several solution-state techniques like NMR, VCD, and ROA as (−)-(4aS, 6R,8aS)-galantamine (274) (Figure 78).…”

Section: Nitrogenated Compoundsmentioning

confidence: 93%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Nitrogenated Compoundsmentioning

confidence: 93%

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Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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“…Caulindole C, 3 a C3 reverse-prenylated indole alkaloid, shows antifungal and antimalarial activities. Flustramine B, 4 a cyclized N-and C3-prenylated tryptamine derivative, exhibits smooth-muscle relaxant activity. Bearing 2-reverse prenyl and 7-prenyl groups on indole core, Notoamide S 5 is a common precursor for the biosynthesis of diverse bioactive metabolites in the genus Aspergillus.…”

Section: Synpacts Synlettmentioning

confidence: 99%

Isoprene: A Promising Coupling Partner in C–H Functionalizations

Zhang

2020

Synlett

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Five-carbon dimethylallyl units, such as prenyl and reverse-prenyl, are widely distributed in natural indole alkaloids and terpenoids. In conventional methodologies, these valuable motifs are often derived from substrates bearing leaving groups, but these processes are accompanied by the generation of stoichiometric amounts of by-products. From an economical and environmental point of view, the basic industrial feedstock isoprene is an ideal alternative precursor. However, given that electronically unbiased isoprene might undergo six possible addition modes in the coupling reactions, it is difficult to control the selectivity. This article summarizes the strategies we have developed to achieve regioselective C–H functionalizations of isoprene under transition-metal and acid catalysis.1 Introduction2 Catalytic Coupling of Indoles with Isoprene3 Catalytic Coupling of Formaldehyde, Arenes and Isoprene4 Catalytic Coupling of 4-Hydroxycoumarins with Isoprene5 Catalytic Coupling of Cyclic 1,3-Diketones with Isoprene6 Conclusion and Outlook

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Synthesis of 2‐Oxindoles from Substituted Indoles by Hypervalent‐Iodine Oxidation

et al. 2018

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A practical conversion of indoles into the corresponding 2‐oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2‐oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

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Formal synthesis of (−)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality

Cited by 13 publications

References 45 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Isoprene: A Promising Coupling Partner in C–H Functionalizations

Synthesis of 2‐Oxindoles from Substituted Indoles by Hypervalent‐Iodine Oxidation

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