Synthese der vier isomeren Hexadecadien‐(10.12)‐ole‐(1)

Truscheit, Ernst; Eiter, K.

doi:10.1002/jlac.19626580106

Cited by 69 publications

(13 citation statements)

References 10 publications

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“…Preservation of double bond geometry of (2) or (E)-allylic phosphonium salts during the Wittig reaction has been demonstrated before e.g. by Truscheit & Eiter [12] unit by non-stereoselective C(3,4) double bond formation. (E)-2-Octenal 12 [14] and propylidenetriphenylphosphorane [7] yielded the undecatrienes 1 a and 1 c (3 : 2 ratio ; 23% yield), the (E)-double bond in the aldehyde being preserved in the products.…”

Section: 2mentioning

confidence: 84%

The Four Isomeric 1,3,5‐Undecatrienes. Synthesis and configurational assignment

Näf

Decorzant

Thommen

et al. 1975

Helvetica Chimica Acta

111

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The four geometrical isomers of 1,3,5-undecatriene, l a 4 have been prepared (stereospecifically and non-stereospecifically), using either (1) the Wittig reaction, (2) thermal sigmatropic hydrogen shifts, (3) partial reduction of triple bonds by zinc, or (4) organocopper reagents. The thermal behaviour of the four 1,3,5-undecatrienes has been investigated and the products formed have been characterized. The spectra of la-d, and of related compounds, have been discussed in order to corroborate their configurational assignment. 1. Introduction. -Some 1,3,5-undecatrienes isolated from the essential oils of both 4. 58; d x d; J = 16; J ' = 7 4. 58; d; J = 7 2.8; d x d; J = 21; J'=12 2. a; d; J = 21 2 . 8 ; d; J = 12 4 . 6 3 ; d x d; J = 15; J ' = 7 4. 63; d; J = 7 5. 58; 12-line system 5. 58; d x t; J = 15; J' = 7 5. 56; d x d; J = 15; J ' = 6 5. 56; d; J = l! 5.33; dxdxt; J = 15; J ' = 6; J I I = 7 5. 33; d x t; J = 1 5 ; J 1 = 7 5.42; d x d; J = 14; J ' = 11 5. 42; d x d; 5.14; J ' = U 5.42; d x d; J = 14; J'= 11 5.96; dxdxt; 5=15; J ' = 6; J I I = 7 5. 96; d x t; J = 15; J ' = 7 5. 07; d with fine splitting; J = 8 / 5.1; d with fine splitting; J = 17 4. 03; d x d; J 10; J' = 2/ 4. 29; d x d; J = 17; J' = 2 4. 03; d; J = 2/ 4. 29; d; J = 2 4.03; d x d ; J = 10; J'= 21 4.29; d x d ; J = 17; J ' = 2Summary. I n the adult male cecropia moth, l-[14C]-propionate is incorporated specifically into juvenile hormone I (1). By chemical degradation it was found that only C(7) and C(11) are labelled, each carbon atom bearing 50% of the radioactivity originally present in J H -I . It is concluded that propionate serves as a precursor of homomevalonate, which in turn is a precursor for J H -I . Application of 2-[W]-propionate and 3-[14C]-propionate leads to extensive randomization of the label. Apparently propionate is metabolized such that C(2) and C(3) can be reused as smaller fragments-probably acetate-while C(l) is either highly diluted or removed from the propionate in a metabolically inactive form.The insect juvenile hormones I and I1 ( J H -I , 1; JH-11, 2 ) are the only known terpenoid compounds where methyl groups biosynthetically derived from C(3') of mevalonate are formally replaced by ethyl groups. They were discovered in adult males of the saturniid moth Hyalophora cecropia [l] [Z] and were also isolated from the related species Hyalophora gloveri [3] and Samia Cynthia [4]. Juvenile hormone is produced by corpora allata, a pair of glands associated with the insect brain. It was *

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Section: 2mentioning

confidence: 84%

The Four Isomeric 1,3,5‐Undecatrienes. Synthesis and configurational assignment

Näf

Decorzant

Thommen

et al. 1975

Helvetica Chimica Acta

111

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“…Conjugated enynes have also been prepared by dehydration of \t-ynols (202,213,217,224), by Wittig reaction (213), via vinyl copper intermediates (225) (Scheme 87), and from alkenyl boranes (see below). The acetylene can be reduced to a Zolefin with Lindlar catalyst (213,217,226) or preferably via hydroboration-protonolysis (223,224,227), or to an E-olefin with lithium aluminium hydride (225).…”

Section: Scheme 85mentioning

confidence: 99%

“…Reactions between an (X,~-unsaturated aldehyde and a saturated Wittig reagent (71,(202)(203)(204)(205)(206)(207)(208)(209) or a saturated aldehyde and an olefinic (202,(210)(211)(212) or acetylenic (213) Wittig reagent have been utilized for elaborating the conjugated dienyl system. By varying the solvent systems and reaction conditions, some control over EIZ ratios can be exercised.…”

Section: Scheme 82mentioning

confidence: 99%

Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application

Brand

Young²,

Silverstein

1979

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…38 mg, ubereinstimmend rnit dem Ausgangsmaterial 12. ( 15,: Aus 400 mg (1.27 mmol) 6 ') wird das Thioacetal wie vorstehend gewonnen; Schmp. 139-141 "C (aus Ether), Ausb.…”

Section: -Aceto~v-f5j6-dimetho~~~-cis-er~~~~~inan-j-en-8-onunclassified

Synthetische Arbeiten in der Reihe der aromatischen Erythrina‐Alkaloide, XXIII. 1,7‐Cyclo‐cis‐erythrinane

Mondon¹,

Vilhuber²,

Fischer³

et al. 1979

Chem. Ber.

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Durch Erhitzen der Bromverbindung 13 mit Kaliumhydroxid in Diethylenglycol auf 180-C entsteht das 1,7-Cyclo-cis-erythrinan-Derivat 17. Nach Hydrolyse zum Keton 18 erhalt man durch Umwandlung der Ketogruppe die Cycloverbindungen 19 -21 und 27 -33. Reduzierende Bedingungen spalten den Cyclopropanring sehr leicht auf unter Bildung des Olefinlactams 10 oder des gesattigten Lactams 1. Uber das Cycloolefin 35 gelingt die Darstellung von 37 und der zugehorigen Base 38 mit dem Grundgerust der 1,7-Cyclo-cis-erythrinane. Syntheses of Aromatic Erythrina Alkaloids, XXIII" 1,7-Cyclo-cis-erythrinanesThe 1,7-cyclo-cis-erythrinane derivative 17 is formed by heating the bromo compound 13 with potassium hydroxide in diethylene glycol to 18O'C. Hydrolysis of 17 yields the ketone 18 which, by reactions of the carbonyl group, is transformed into the cyclic compounds 19-21 and 27-33. The cyclopropane ring is easily cleaved by reduction to give the unsaturated lactam 10 or the saturated lactam 1. The 1,7-cyclo-cis-erythrinane structures 37 and 38 can be synthesized by way of the cyclic olefin 35. Entwicklung eines SyntheseplansSpirocyclische Funfringlactame der cis-Erythrinanreihe vom Typus 1 zeigen vielfach anomale Reaktionsweisen, z. B. gelingt es nicht, aus dem Bromketolactam 2 durch Abspaltung von Bromwasserstoff das ungesattigte Ketolactam bzw. dessen Enolform 4 zu erhalten. Beim Kochen von 2 in Collidin entsteht nur das Enollactam 5 und daneben Collidinhydrobromid, wobei der zur Reduktion benotigte Wasserstoff aus dem Collidin stammt'). Erhitzt man 2 in einer Losung von Kaliumhydroxid in Diethylenglycol, so wird das Brom unter Umkehr gegen die Hydroxygruppe ausgetauscht unter Bildung der als Ketol-A bezeichneten Verbindung 3 der trans-Erythrinanreihe *).Als Ausgangsmaterial zur Darstellung ungesattigter b'(@-Erythrinanderivate schien auch das fruher beschriebene 2-Keto-cis-lactam 6 3, geeignet zu sein. In dieser Verbindung ist aul3er C-1 auch C-3 aktiviert, das bei den naturlichen Erythrinanen stets eine Methoxyoder Hydroxygruppe tragt. Zur Prufung der Reaktivitat der der Ketogruppe benachbarten 0 Verlag Chemie, GrnbH, D-6940 Weinheirn, 1979

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Synthese der vier isomeren Hexadecadien‐(10.12)‐ole‐(1)

Cited by 69 publications

References 10 publications

The Four Isomeric 1,3,5‐Undecatrienes. Synthesis and configurational assignment

The Four Isomeric 1,3,5‐Undecatrienes. Synthesis and configurational assignment

Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application

Synthetische Arbeiten in der Reihe der aromatischen Erythrina‐Alkaloide, XXIII. 1,7‐Cyclo‐cis‐erythrinane

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