Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

Pichlmair, Stefan; Ruiz, Manuel de Lera; Vilotijević, Ivan; Paquette, Leo A.

doi:10.1016/j.tet.2006.03.066

Cited by 14 publications

(9 citation statements)

References 28 publications

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“…Methanolysis to 34 and then hydrogenolysis in the presence of (BOC) 2 O gave N -BOC alcohol 13a . For investigation of trans/cis amide preferences, alcohol 13a was converted to the N -acylbenzoate 18 36 and this was converted by methanolysis to the alcohol 13b .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and Anti-3-Fluoro- and 3-Hydroxypyrrolidines

et al. 2011

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N-Acetylmethanopyrrolidine and its four 5-syn/anti-fluoro and hydroxy derivatives have been synthesized from 2-azabicyclo[2.2.0]hex-5-ene, a 1,2-dihydropyridine photoproduct. These conformationally constrained mimics of idealized Cβ-gauche and Cβ-anti conformers of pyrrolidines were prepared in order to determine the inherent bridge bias and subsequent heteroatom substituent effects upon trans/cis amide preferences. The bridgehead position and also the presence of gauche(syn)/anti-5-fluoro or 5-hydroxy substituents have minimal influence upon KT/C values of N-acetylamide conformers in both CDCl3 (43–54% trans) and D2O (53–58% trans). O-Benzoylation enhances the trans amide preferences in CDCl3 (65% for a syn-OBz, 61% for a trans-OBz) but has minimal effect in D2O. The synthetic methods developed for N-BOC-methanopyrrolidines should prove useful in the synthesis of more complex derivatives containing α-ester substituents. The KT/C results obtained in this study establish baseline amide preferences that will enable determination of contributions of α-ester substituents to trans-amide preferences in methanoprolines.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and Anti-3-Fluoro- and 3-Hydroxypyrrolidines

et al. 2011

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“…Many unnished efforts have been made for the total synthesis of this kind of compounds. [337][338][339][340] For instance, Uemura and co-workers in 2004 reported the total synthesis of core structure of mangicols A 504 in twenty-nine steps employing a Diels-Alder reaction of a macrocycle. 337 In 2012, Yu and co-workers 14,15,56,58,341 designed and effective pathway to obtain the spirotricyclic core analogue of mangicol A.…”

Section: Sesquiterpenesmentioning

confidence: 99%

Application of Pauson–Khand reaction in the total synthesis of terpenes

Heravi

Mohammadi

2021

RSC Adv.

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“…(Scheme 2). Briefly, known 3, prepared from citronellol (Pichlmair et al, 2006), was epoxidized with m-chloroperbenzoic acid, and the resulting epoxide treated with periodic acid to give aldehyde 4. Addition of Grignard reagent, prepared from 2-bromo-1-butene to 4, afforded allylic alcohol 5, which was subjected to Johnson-Claisen rearrangement to provide ester 6.…”

Section: Coupled Gas Chromatographic-electroantennographic Detection mentioning

confidence: 99%

2,3-Dihydrohomofarnesal: Female Sex Attractant Pheromone Component of Callosobruchus rhodesianus (Pic)

et al. 2010

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Callosobruchus rhodesianus (Pic) (Coleoptera: Chrysomelidae: Bruchinae) is a pest of stored legumes through the Afro-tropical region. In laboratory bioassays, males of C. rhodesianus were attracted to volatiles collected from virgin females. Collections were purified by various chromatographic techniques, and the biologically active component isolated using gas chromatographic-electroantennographic detection analysis. Gas chromatography-mass spectrometry and NMR analyses suggested that the active compound was 2,3-dihydrohomofarnesal, i.e., 7-ethyl-3,11-dimethyl-6,10-dodecadienal. The structure was confirmed by non-stereoselective and enantioselective total synthesis. Using chiral gas chromatography, the absolute configuration of the natural compound was confirmed as (3S,6E)-7-ethyl-3,11-dimethyl-6,10-dodecadienal. Y-tube olfactomter assays showed that only the (S)-enantiomer attracted males of C. rhodesianus. The (R)-enantiomer and racemate did not attract males, suggesting that the (R)-enantiomer inhibits the activity of the natural compound. In combination with previous reports about sex attractant pheromones of congeners, we suggest that a saltational shift of the pheromone structure arose within the genus Callosobruchus.

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Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

Cited by 14 publications

References 28 publications

Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and Anti-3-Fluoro- and 3-Hydroxypyrrolidines

Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and Anti-3-Fluoro- and 3-Hydroxypyrrolidines

Application of Pauson–Khand reaction in the total synthesis of terpenes

2,3-Dihydrohomofarnesal: Female Sex Attractant Pheromone Component of Callosobruchus rhodesianus (Pic)

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