Terpenoids—XLVI

Narayanan, C. S.; Kulkarni, Kiran; Vaidya, Ashwin; Kanthamani, S.; Kumari, G.Lakshmi; Bapat, B.V.; Paknikar, S.K.; Kulkarni, S.N.; Kelkar, G.R.; Bhattacharyya, S.C.

doi:10.1016/s0040-4020(01)98430-3

Cited by 30 publications

(9 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The patchoulenes 130–133 and seychellenes 134 and 135 have been reported to co‐occur with 129 in several species, [307, 332, 334–336, 338, 339] and also many of these compounds are observed as products of the patchoulol synthase, [22, 290] supporting their common biosynthesis through shared intermediates (Scheme 35 A) and corresponding absolute configurations. Formally, the absolute configuration of 130 ([α] D 30 =−42.6, c 10.51, CHCl 3 ) was specified by chemical correlation with patchouli alcohol through acid treatment, at a time when 129 b was believed to be the correct structure of this sesquiterpene alcohol.…”

Section: Cyclised and Rearranged Guaianesmentioning

confidence: 92%

“…Al ater synthesis from (R)-carvone (ent-38) resulted in (À)-129 ([a] D 25 = À121.3, c 2.3, CHCl 3 ). [331] Compound (À)-129 was also isolatedf rom plants of the genera Valeriana [332][333][334] and Nardostachys [335,336] The complete 13 CNMR data of 129 are available. [290,333,337] The patchoulenes 130-133 and seychellenes 134 and 135 have been reported to co-occur with 129 in severals pecies, [307, 332, 334-336, 338, 339] and also many of these compounds are observed as products of thep atchoulol synthase, [22,290] supporting their commonb iosynthesis through shared intermediates (Scheme 35 A) and correspondinga bsolutec onfigurations.…”

Section: Compounds From J1mentioning

confidence: 99%

“…A later synthesis from ( R )‐carvone ( ent ‐38) resulted in (−)‐ 129 ([α] D 25 =−121.3, c 2.3, CHCl 3 ) [331] . Compound (−)‐ 129 was also isolated from plants of the genera Valeriana [332–334] and Nardostachys [335, 336] The complete 13 C NMR data of 129 are available [290, 333, 337] …”

Section: Cyclised and Rearranged Guaianesmentioning

confidence: 99%

See 2 more Smart Citations

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

View full text Add to dashboard Cite

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.

show abstract

Section: Cyclised and Rearranged Guaianesmentioning

confidence: 92%

Section: Compounds From J1mentioning

confidence: 99%

See 1 more Smart Citation

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…-MS. : M+ 204 (13,7) NMR.-Spektrum: CH,-= 0,84 ppni (d, J = 7 Hz); Curcwneiz, das cbcnfalls in Fraktion 1 angereichcrt war, hatte eine optischc Rotation von [a];: = + 37,7" (c = 0,7, CHCI,). Die bckannten Wertc schwankcn zwischen + 36,2 und 40" (CHCI,) [I81 [all[22]. Fur scin Enantiomeres wurde die Konstante init -30,l' (CH,OH) angegebcn[23].…”

unclassified

Parmon, eine Phantomverbindung im Veilchenblütenöl

Uhde

Ohloff

1972

Helvetica Chimica Acta

View full text Add to dashboard Cite

Summary. 86% of the volatile fraction of a violet flower extract are made up by 12 compounds. 10 of these were previously unknown. Ruzicka's parmon was shown to be (+)-a-ionone.Uas Bliitenol des Parma-sowic des Viktoria-Veilchcns gehorte am Anfang unseres Jahrhunderts zu den kostbarsten Ingredienzien der feinen Parfiimerie. Sein Wohlgeruch faszinierte jedoch nicht nur die Noblen der damaligen Haute-VolCe, sondern es regtc ebenfalls in segensreicher Weise die Phantasie des Naturstoffchemikers jener Epoche an1

show abstract

“…(The last compound is derived formally, albeit not experimentally, from patchouli alcohol by a 1,2-methyl migration.) The compounds 3, 4, 5, and 7patchoulene (7) have been isolated from Indian valerian root oil (from Valeriana wallichii) (Narayanan et al, 1964); ßpatchoulene (5) is present in minor quantity in guaiac wood oil (from Bulnesia sarmienti) (Bates and Slagel, 1962a); while cyperene (8) (Trivedi et al, 1964b), patchoulenone (9) (Motl et al, 1963;Trivedi et al, 1964a), cyperotundone (isopatchoulenone, cyperenone) (10) (Hikino et al, 1965(Hikino et al, , 1966(Hikino et al, , 1967b; Naves and Ardizio, 1954; Couchman et al, 1964;Nerali et al, 1965), patchoulenol (11) (Nerali and Chakravarti, 1967), cyperenol (12) (Nerali et al, 1965), sugeonol acetate (13) (Hikino et al, 1968a), and sugetriol triacetate (14) (Hikino et al, 1967a) have been isolated from the oils of tuber of nutgrass (Cyperus rotundus) and tuber of cyperus (Cyperus scariosus and Cyperus articulatus) (Figure 1).…”

mentioning

confidence: 99%