An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol†

The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework.

Chiral synthons from carvone, Part 40. A simple, enantiospecific approach to both enantiomers of 1 alpha,25-dihydroxyvitamin D-3 A-ring precursors from R-carvone

A simple and direct approach to both enantiomeric series of A-ring derivatives of 1 alpha,25-dihydroxyvitamin D-3 and the corresponding 1 alpha,3 alpha-derivatives, starting from the abundantly available R-carvone, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

Enantiospecific total synthesis of (+)-pinguisenol 1, a sesquiterpene containing a cis-1,2,6,7-tetramethylbicyclo[4.3.0]nonane carbon framework incorporating two vicinal quaternary carbon atoms and four cis-oriented methyl groups on four contiguous carbon atoms, isolated from a liverwort, is described. The orthoester Claisen rearrangement of the allyl alcohol 9, obtained from (R)-carvone, generates the ester 12. Intramolecular cyclopropanation of the diazo ketone 13, derived from the ester 12, furnishes the tricyclic ketone 7. Degradation of the isopropenyl group followed by regioselective reductive cyclopropane ring cleavage transforms compound 7 into the hydroxy ketone 21. Wolff–Kishner reduction of the hydroxy ketone 21 followed by oxidation and Grignard reaction furnishes pinguisenol (+)- 1.

Chiral Synthons from Carvone. Part 10. Synthesis of (+)-(1S,3S,4S,7S, 8R)-5,7-Dimethyl-10-oxatetracyclo-(5.3.0.03,5,04,8)decan-9-one.

Degradation of the tolyl group in the tricyclic ketone 1b followed by stereospecific reduction of the resultant ketoester (6) furnishes the title compound (4) containing a new tetracyclic framework, establishing the stereochemistry of the aryl group in 1.

Chiral synthons from carvone .20. Stereo- and enantiospecific total synthesis of (-)-valeranone

Stereo- and enantiospecific total synthesis of the irregular sesquiterpene, valeranone, starting from S-6-methylcarvone employing a hydrindanone to decalone ring expansion methodology, is described.

Enantioselective synthesis of both (+)- and (-)-derivatives of bicyclo[4.3.0]nonan-8-one and 3,8-diones from R-carvone

Enantioselective synthesis of both the enantiomeric forms of the hydrindane derivatives mentioned in the title, potential chiral precursors in terpenoid synthesis, starling from R-carvone employing two different cyclopentannulation methodologies is described.

Synthesis of taxanes - The carvone approach; A simple, efficient stereo- and enantio-selective synthesis of the functionalised A ring

A highly stereo- and enantio-selective methodology for the construction of the chiral functionalised A-ring of taxanes, starting from (R)-carvone employing a short, simple and efficient sequence is described.

Chiral synthons from carvone. Part 53. First enantiospecific synthesis of (-)-9-pupukeanone

The first enantiospecific total synthesis of (-)-9-pupukeanone, starting from (R)-carvone employing a combination of Michael-Michael reaction and an intramolecular rhodium carbenoid C H insertion reaction as key steps, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

Chiral synthons from carvone, Part 56. Enantiospecific synthesis of (-)-4-thiocyanatoneopupukeanane

Enantiospecific total synthesis of the natural enantiomer of the marine sesquiterpene (-)-4-thiocyanatoneopupukeanane (6) is described. The bicyclo[2.2.2]octanonecarboxylate 11, obtained from (R)-carvone and methyl methacrylate via Michael-Michael reaction, was transformed into bicyclo[2.2.2]octenecarboxylic acid 8. Intramolecular cyclopropanation reaction of the diazo ketone 7, derived from the acid 8, followed by regioselective reductive cyclopropane ring cleavage generated neopupukeanol 20, which was transformed into (-)-4-thiocyanatoneopupukeanane 6.

A versatile, RCM based approach to eudesmane and dihydroagarofuran sesquiterpenoids from (-)-carvone: a formal synthesis of (-)-isocelorbicol

An enantiospecific and diversity oriented approach to a range of functionalized eudesmane, nor-, iso-, and dihydroagarofuran frameworks from (-)-carvone is delineated. The cornerstone of this approach is the installation of the quaternary carbon center through reductive opening of the carvone epoxide and setting-up of RCM reaction to generate the bicyclic eudesmane framework. Various options like carbocation mediated oxycyclization and intramolecular hydroxy directed epoxide opening have been explored for the construction of the bridged tetrahydrofuran moiety. Among the several eudesmane and dihydroagarofurans accessed during the present study, one has been previously elaborated to iso-celorbicol, thus constituting its formal synthesis. (C) 2015 Elsevier Ltd. All rights reserved.

An enantiodivergent protocol from R-(-)-carvone: synthesis of dihydroagarofuran sesquiterpenoid 1-deacetoxy-ent-orbiculin A

A strategy for achieving enantiodivergency from R-(-)-carvone in the context of synthesis of eudesmanes and dihydroagarofurans is disclosed, which involves, among other things, sequential setting of the C10 quaternary centre and recreation of the desired C7 isopropyl stereochemistry to enter the antipodal series. A synthesis of 1-deacetoxy-ent-orbiculin has been achieved as a demonstration of the effectiveness and applicability of this approach. (C) 2015 Elsevier Ltd. All rights reserved.

Combined action of S-carvone and mild heat treatment on Listeria monocytogenes Scott A

The combined action of the plant-derived volatile, S-carvone, and mild heat treatment on the food-borne pathogen, Listeria monocytogenes, was evaluated. The viability of exponential phase cultures grown at 8 °C could be reduced by 1·3 log units after exposure to S-carvone (5 mmol l−1) for 30 min at 45 °C, while individual treatment with S-carvone or exposure to 45 °C for 30 min did not result in a loss in viability. Other plant-derived volatiles, namely carvacrol, cinnamaldehyde, thymol and decanal, were also found to reduce the viability of L. monocytogenes in combination with the same mild heat treatment at concentrations of 1·75 mmol l−1, 2·5 mmol l−1, 1·5 mmol l−1 and 2 mmol l−1, respectively. These findings show that essential oil compounds can play an important role in minimally processed foods, and can be used in the concept of Hurdle Technology to reduce the intensity of heat treatment or other individual hurdles.

Effect of substrata on the development of stem cuttings of Lippia alba (Mill.) NEBR. - Limonene-carvone chemotype

Studies were conducted to show the effect of different substrata on the development of stem cuttings of Lippia alba made of limonene-carvone chemotype. The experiment was done in the College of Agronomical Sciences, UNESP, Botucatu, SP, Brazil in 2000. The cuttings were planted in polystyrene trays consisting of 72 cells. The cuttings had about 0.20 m of length and were put in the following substrata:Fine sand (T1), commercial substratum (T2), carbonised rice peel and local soil (T3), local soil, cow manure and carbonised rice peel (T4), vermiculite (T5), and carbonised rice peel (T6). After 40 days the development of stem cuttings were evaluated. High rate of rooting of stem cuttings was verified, with average of 95 10 and no significant difference between the treatments. In relation to dry mass of aerial parts and dry mass of roots, significant differences were found. For dry mass production of aerial parts the commercial substratum (T2) and the local soil, cow manure, carbonised rice peel (T4) were optimal. For mass of roots the local soil, cow manure, carbonised rice peel (T4) proved to be the best.