Synthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups

Booker‐Milburn, Kevin I.; Jenkins, Helen; Charmant, Jonathan P. H.; Mohr, Peter J.

doi:10.1021/ol035373u

Cited by 33 publications

(20 citation statements)

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“…For 118 this discussion is hypothetical, because this compound was only obtained in racemic form by synthesis and is not known as natural product. [299] The hydrocarbons( + +)-115 and( + +)-116 were both isolated only from the fruits of Peucedanum tauricum. [311] Their co-occurrencei no ne organisms uggests that they may have the same cationic precursor J3.T he absolute configurations of 115 and 116 were specified by comparison of their hydrogenation products to those obtained from (+ +)-g-gurjunene (120, Scheme 30 B), [312] leading to one common product (119a)f rom all three materials, as judged by GC analysisu sing two different chiral stationary phases.…”

Section: Guaianes Formedf Romcationsj3a Nd J4mentioning

confidence: 99%

“…[293] As ubsequent synthesis of the reported structures 104 and 105 for pogostol and its methyl ether demonstrated that both assignments were erroneous. [299] Amand et al then gave ac orrection as 103. [295] Althoughp ogostoli sl ong known and fairly widespreadi n Nature,t he absolutec onfigurations till remains to be determined.F or unclear reasons the structure of ent-103 has been assigned to the CAS number of pogostol (21698-41-9), while in fact 103 may be more likely, because this corresponds to the main product 106 of the patchoulol synthasef rom P. cablin that also makes 103 as as ide product.…”

Section: Guaianes Formed Fromcationsj1a Nd J2mentioning

confidence: 99%

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Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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Section: Guaianes Formedf Romcationsj3a Nd J4mentioning

confidence: 99%

Section: Guaianes Formed Fromcationsj1a Nd J2mentioning

confidence: 99%

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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“…In the same year the structures for pogostol and its methyl ether were challenged by Booker‐Milburn et al after their total synthesis . On the basis of 13 C‐NMR data, they proved that natural pogostol was neither identical to H nor to its 7‐epimer.…”

Section: Analytical Investigations Of Patchouli Essential Oilmentioning

confidence: 99%

The essential oil of patchouli,Pogostemon cablin: A review

Beek

Joulain²

2017

Flavour & Fragrance J

122

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The leaves of Pogostemon cablin (Blanco) Benth. (Lamiaceae) are the source of patchouli essential oil, which is -with an annual production of about 1300 tonnes -an important and unique commodity in the fragrance industry. All the literature pertaining to patchouli was critically reviewed with an emphasis on the qualitative and quantitative chemical analysis of the oil but also harvesting, fermentation, drying, distillation, used analytical techniques, sensory aspects including molecules responsible for the odour, adulteration and toxicological aspects, i.e., skin sensitisation, are discussed. In total 72 constituents have been convincingly identified in the oil and another 58 tentatively. The main constituent is the sesquiterpene patchoulol. For this review over 600 papers were consulted and in the supplementary information all patchouli-related references not relevant enough to be cited in the paper itself are listed. 6 It has been stated that "this oil is one of the most important materials available to the perfumer." 7 Approximately 90% of today's global production of 1200-1300 metric tonnes per annum is realised in Indonesia. --------------------------------------------------------------------------------------------------------------------------------This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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“…Unfortunately, published mass spectra and retention indices for all other stereoisomers of pogostol and of globulol were not available, so these compounds were also candidate structures for X . The 13 C NMR data for all five compounds16–20 and the two pogostol stereoisomers ( 11 and 12 )21 have been reported, and therefore we strived to confirm the identities of X and 10 by obtaining 13 C NMR data for X by CLSA‐NMR (note: the originally published structure of 10 22 was later found to be incorrect21 and then corrected;23 in ref. 17 the wrong structure is shown for 13 ).…”

Section: Methodsmentioning

confidence: 99%

Copper Substitution and Mixed Cation Effect in Ag₁₀Te₄Br₃

Giller

Bawohl

Gerstle

et al. 2013

Zeitschrift anorg allge chemie

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Abstract. Ag 10 Te 4 Br 3 is the first compound of this substance class, where covalent interactions in the tellurium substructure led to the formation of Peierls distorted linear chains, responsible for a strong modulation of the electronic structure. This compound represents the first example within a series of pnp switching compounds, where the interplay of mobile ions, in combination with the attractive interactions, created by partially covalent-bonded anion substructures defines

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Synthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups

Cited by 33 publications

References 19 publications

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

The essential oil of patchouli,Pogostemon cablin: A review

Copper Substitution and Mixed Cation Effect in Ag₁₀Te₄Br₃

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Synthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups

Cited by 33 publications

References 19 publications

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

The essential oil of patchouli,Pogostemon cablin: A review

Copper Substitution and Mixed Cation Effect in Ag10Te4Br3

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Copper Substitution and Mixed Cation Effect in Ag₁₀Te₄Br₃