Improved synthesis of 2-methyl-6-methylene-2,7-octadien-4-ol, a pheromone of Ips paraconfusus, and an alternative synthesis of the intermediate, 2-bromomethyl-1,3-butadiene

Riley, Robert G.; Silverstein, Robert M.; Katzenellenbogen, John A.; Lenox, Ronald S.

doi:10.1021/jo00927a040

Cited by 42 publications

(14 citation statements)

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“…In 1974, Silverstein, Katzenellenbogen et al [14] . reported the synthesis of ipsdienol ( II ) by reaction of 2‐(bromomethyl)buta‐1,3‐diene ( 2 ) with Zn followed by treatment with 3‐methyl‐2‐butenal, in 65 % yield, following the same methodology that Katzenellenbogen and Lenox have proposed for the synthesis of ipsenol ( I ) [27] .…”

Section: Synthesis Of (±)‐Ipsenol and (±)‐Ipsdienolmentioning

confidence: 99%

“…In overall, the main merit of this work is that the organozinc species III , as a “isoprene synthon”, could be obtained in one step from 1,4‐dibromo‐2‐(bromomethyl)but‐2‐ene ( 1 ), resulting in a new and simple method for the incorporation of the isoprenyl motif, very competitive respect to other reported protocols using other metalated species (potassium, boron, tin, or silicon) [14] . Molecules bearing the isoprenyl group are starting materials for the Diels‐Alder reaction, and are largely present in natural products.…”

Section: Synthesis Of (±)‐Ipsenol and (±)‐Ipsdienolmentioning

confidence: 99%

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The Synthesis of Ipsenol and Ipsdienol: A Review (1968–2020)

Marco‐Contelles

2021

The Chemical Record

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Herein I present a review on the synthesis of ipsenol and ipsdienol, two aggregation pheromones of bark beetles, isolated from different species of genus Ips, and serious pests of conifer forests. I have covered the literature for around fifty years, since 1968 to 2020. This account has been divided in different sections and sub‐sections, including a general and brief outlook on their isolation, structure and biological activity, to continue with the reported synthesis of racemic ipsenol and ipsdienol, including my own contribution to topic, and the presentation of reports describing the synthesis of enantiomerically pure ipsenol and ipsdienol. Particular attention has been devoted to identify and highlight racemic or enantiomerically pure “isoprene synthons”, and isoprenylation methods employed in the synthesis of ipsenol and ipsdienol, of general interest for related terpene derivatives synthesis.

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Section: Synthesis Of (±)‐Ipsenol and (±)‐Ipsdienolmentioning

confidence: 99%

Section: Synthesis Of (±)‐Ipsenol and (±)‐Ipsdienolmentioning

confidence: 99%

The Synthesis of Ipsenol and Ipsdienol: A Review (1968–2020)

Marco‐Contelles

2021

The Chemical Record

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“…GC. gereinigte Probe zeigte eine Drehung von 1= 1 dm (7) Clfi15NOz (181,23) Ber. C 66,27 H 8,34 N 7,73% Gef.…”

Section: N a O E T L Etohunclassified

“…6:2: 1 auf, die unmittelbar vor Methyleugenol eluiert wurden. Die sich stark gleichenden Massenspektren -neben m / t 91 und 92 trat die Serie m/z 181,164,149,134,122 phellandrene (A und B; X = N02)2), und die eher ungewohnlichen Massenspektren konnten nun auf die in Schema 1 skizzierte Weise erklart werden.…”

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Neue Phellandren‐Derivate aus dem Wurzelöl von Angelica archangelicaL

Escher

Keller

Willhalm

1979

Helvetica Chimica Acta

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Summary 2-Nitro-1,5-p-menthadiene (5), trans-and cis-6-nitro-1 (7), 2-p-menthadiene (6 and 7), trans-1 (7), 5-p-menthadien-2-yl acetate (9) and a formal phellandrene derivative, 7-isopropyl-5-methyl-5-bicyclo[2. Die Destillationsfraktion wurde mittels Adsorptions-Chromatographie an Aluminiumoxid von den Kohlenwasserstoffen befreit und die polaren Anteile an Kieselgel weiter aufgetrennt. Die unpolarste Zone (0,14% des 01s) wurde durch praparative Gas-Chromatographie in zwolf Fraktionen unterteilt. Die neuen Inhaltsstoffe (5-7, 9 und 16l)) wurden mit Hilfe von ein bis zwei gas-chromatographischen Operationen isoliert und anhand von 'H-NMR.-und Massenspektren charakteri- I)Die Formeln 5-7, 9 und 16 stehen im Zusammenhang mit den Verbindungen aus dem Angelica-01 fur eines der beiden Enantiomeren oder fur das Racemat.

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“…SILVERSTEIN et al (51,136) began with the dithiane derivative of 3-methyl-2-butenal (260) and proceeded as in Scheme 47. RILEY et al (142) coupled (260) with (237) in the presence of zinc, and KARLSEN et al (138) coupled (244) Scheme 53…”

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confidence: 99%