Total Synthesis of Sequiterpenes

Heathcock, Clayton H.

doi:10.1002/9780470129654.ch2

Cited by 14 publications

(1 citation statement)

References 310 publications

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“…Molecules bearing a tertiary (or quaternary) benzylic stereocenter are widely representated in natural products and pharmaceuticals (Figure ). Curcumene 1 , curcuhydroquinone 2 , ar -turmerone 3 and congeners, and members of the bisabolane sesquiterpenes family have been used in traditional medicine, exhibit anticancer/antimicrobial activities, and are also employed in cosmetics . ( S )- ar -Himachalene 4 is a key component in cedar wood essential oils, whereas the R -enantiomer is a male-specific pheromone of some flea beetles .…”

Section: Introductionmentioning

confidence: 99%

Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene

2017

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A straightforward strategy for the syntheses of curcumene and ar-himachalene is reported. Synthetic highlights include a catalytic and asymmetric vinylogous Mukaiyama reaction and a stereospecific hydrogenolysis of a tertiary benzylic center using Pd/C or Ni/Raney catalysts. Notably, using Ni/Raney, the stereoselectivity outcome (inversion vs retention) of the hydrogenolysis depends on the tertiary benzylic alcohol substitution.

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Section: Introductionmentioning

confidence: 99%

Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene

2017

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Stereokontrollierte Synthesen von verbrückten Ethern durch Dominocyclisierungen

et al. 1998

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Stereoselektiver Aufbau von trans‐Decalinen über intramolekulare En‐Reaktionen; Synthese des enantiomerenreinen Cadinan‐Sesquiterpens Veticadinol

et al. 1988

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nen nahezu idealen Khombus (Winkelsumme des Vierringes = 359.4'). Das RhZ-Atom ist um 55.7" aus der Ebene eines planaren Funfringes abgeknickt. In bezug auf Formalladungen w2re anstelle von P : " und d8,d6-Rh auch die Alternative P: " und d6,d"-Rh diskutierbar. 4 konnte sich auch aus [($-P,,)RhCp*], einem Sandwichkomplex rnit dem Phosphor-Analogon des Cyclobutadiens als Ligand, durch oxidative Addition (Offnung einer P-P-Kante) gebildet haben. At b. I. Struktur von 4 i m Kristall. Ausgewrihlte Bindungslangen [A\ und -wnkel ["I. R h l -P I 2.381(2), Rhl-P2 2.392(2). Rhl-P3 2.387(2), Rhl-P4 Q VCH ~etIuysyesell.~chuf~ mhH. 0-6940 Weinheirn. 1986 0044-8249/88/0505-0740 S 02.SON Anyew. 5: Veticadinol 2, dessen Slruktur bisher nicht 2.weifelsfrei hewiesen ist, wurde von Chiurdoglu und Delsemme aus kongolesischem Vetiverol isoliert. Der Versuch, 2 in VetiverBl ,,Bourbon", das uns zur Verfiigung geslellt worden war, durch GC-MS-Analyse nach siulenchromatographischer Vorreinigung nachzuweisen, verlief negativ.

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Total Synthesis of Sequiterpenes

Cited by 14 publications

References 310 publications

Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene

Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene

Stereokontrollierte Synthesen von verbrückten Ethern durch Dominocyclisierungen

Stereoselektiver Aufbau von trans‐Decalinen über intramolekulare En‐Reaktionen; Synthese des enantiomerenreinen Cadinan‐Sesquiterpens Veticadinol

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