Stereoselective synthesis of a synthon for the A-ring of taxol from R-(+)-verbenone

Winkler, Jeffrey D.; Bhattacharya, Samit; Liotta, Fina; Batey, Robert A.; Heffernan, Gavin D.; Cladingboel, David E.; Kelly, Robert C.

doi:10.1016/0040-4039(95)00257-d

Cited by 16 publications

(8 citation statements)

References 24 publications

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“…(R)-(+)-Verbenone 273 has been converted into the lactone 285, a synthon for members of the taxane series, 445 and another taxane synthon 286 has been accessed from (+)-pinene 239. 446 Verbenone oxime 287 reacts with sulfuric acid in CH 3 CN to yield the unusual lactam 288 whose structure was determined by X-ray analysis.…”

Section: Pinanesmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1998

Nat. Prod. Rep.

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Species Principal constituents ReferenceAbies balsamea Mill -and -pinene, -phellandrene, limonene Achillea biebersteinii Afan piperitone, or cineol and camphor Aloysia triphylla (L'Herit.) Britton citral, limonene Alpinia conchigera Griff. cineol Alseuosmia macrophylla A. Cunn. flowers: linalool Ambrosia microcephala DC. camphor, bornyl acetate Amomum subulatum Roxb. cineol, -terpineol, -and -pinene Artemisia afra yomogi alcohol, artemisyl acetate Artemisia afra Willd. cineol, terpinen-4-ol, borneol Artemisia ordosica -and -pinene, sabinene Austromyrtus dulcis (C. T. White) L. S. Smith (chemotype) -pinene, cineol Boronia megastigma Nees. -ionone, 8-hydroxylinalyl esters, geranyloxy cinnamate Bouea macrophylla Griff. ( E)--ocimene, -pinene Calamintha cretica piperitenone, piperitenone oxide Calamintha incana (Sm.) Boiss. piperitenone oxide Callistemon speciosus Anthor. cineol, -pinene, -terpineol Canella winteriana Gaertn. stem and bark: cineol, terpinen-4-ol, -terpinyl acetate, -terpineol; leaves: myrcene Cedronella canariensis Webb et Berth. ssp. canariensis pinocarvone Chamelaucium uncinatum genotypes -pinene, citronellal, limonene, linalool, -terpinyl acetate Chenopodium ambrosioides limonene, trans-pinocarveol Chenopodium botrys -8 Chrysanthemum balsamata carvone, camphor Chrysanthemum lavandulaefolium menthol Cinnamomum camphora Nees et Ebermaier camphor, cineol, terpinen-4-ol, limonene Cinnamomum puciflorum -2 Citrus grandis limonene Clausena anisata (Willd.) J. D. Hook limonene, myrcene Coleus aromaticus carvacrol, camphor Coreopsis barteri Oliv. & Hiern limonene, -phellandrene Coreopsis grandis Hogg ex Sweet myrcene Coriandrum sativum seeds: linalool Coridothymus capitatus Reich. f. carvacrol 98, 99 Cunila fasiculata menthofuran Cunila microcephala menthofuran, limonene Curcuma aeruginosa Roxb. cineol, camphor Curcuma amada Roxb. myrcene Curcuma aromatica Salisb. cineol, camphor, isoborneol, camphene Curcuma cochinchinensis Gagnep. cineol Curcuma domestica -phellandrene, cineol, p-cymene, -pinene Curcuma pierreana Gagnep. Rhizome, stem: isoborneol, isobornyl acetate leaf: isoborneol, camphor Croton aubrevillei J. Leonard linalool Croton zambesicus Muell. Arg. linalool Cyclotrichum origanifolium (Labill.) Manden. et Scheng. cis-isopulegone, pulegone, isomenthone, menthol Cymbopogon caesius (Nees et Hook. et Arn.) Stapf. perillyl alcohol, geraniol, limonene Cymbopogon citratus (DC.) Stapf. citral, geraniol, myrcene, -and -pinene Cymbopogon khasianus (Munro ex Hack.) Bor. geraniol, geranyl acetate, linalool Cymbopogon schoenanthus piperitone, limonene Daphne mezereum flowers: linalool, linalyl oxides Echinophora chryantha Freyn et Sint. -phellandrene Egletes viscosa various terpenol acetates Elsholtzia ciliata (Thunb.) Hyland chemotype (a): elsholtzia ketone, -thujone chemotype (b): neral, geranial, limonene

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Section: Pinanesmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1998

Nat. Prod. Rep.

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“…The α-pinene allylic oxidation leads to the production of α,β-unsaturated compounds verbenol and verbenone (Fig. 1), raw materials in the production of flavors, insecticides, therapeutic drugs and food industry [3][4][5][6][7][8][9]. Although verbenone is a constituent of strawberry, raspberry, dill, vervain (20.5 wt.…”

Section: Introductionmentioning

confidence: 99%

Kinetic study of α-pinene allylic oxidation over FePcCl16-NH2-SiO2 catalyst

Becerra

González

Villa

2016

Journal of Molecular Catalysis A: Chemical

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“…Due to their pronounced camphor and mint flavor notes [ 48 ], they are also widely utilized in the food industry and are employed as intermediates in the synthesis of perfume, cosmetics as well as pharmaceuticals. A very important reason for the interest in verbenone as a desirable product is also that it can provide a possible chiral precursor for the asymmetric synthesis of the A-ring of the very effective anticancer diterpene, taxol ® [ 26 , 50 ].…”

Section: Introductionmentioning

confidence: 99%

Bioconversion of α-pinene by a novel cold-adapted fungusChrysosporium pannorum

Trytek

Jędrzejewski

Fiedurek

2015

Journal of Industrial Microbiology and Biotechnology

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The psychrotrophic fungus Chrysosporium pannorum A-1 is reported for the first time as a novel biocatalyst for O2-promoted oxidation of α-pinene. GC–MS analysis indicated that the main products of the reaction were compounds of a high commercial value, verbenol (1) and verbenone (2). Exponentially growing cells (days 2–3) were about twice as active as cells in the late stationary phase in terms of the total concentration of products. The highest yields of 1 and 2 were obtained using three-day and two-day-old mycelia and a medium containing 1.5 and 1 % (v/v) of the substrate, respectively. The optimal time for the bioconversion of α-pinene varied from 1 to 3 days, and depended on the kind of product desired. Most of 1 was produced at a relatively high concentration of 360 mg/L after the first six hours of α-pinene bioconversion [with an average yield of 69 mg/(g dry cell L aqueous phase)]. The oxidative activity of C. pannorum was identified across a wide temperature range of 5–25 °C, 10 °C being the optimum for the production of 1 and 20 °C for the production of 2. Sequential addition of the substrate during 3 days of the biotransformation resulted in a significant increase in 1 and 2 up to 722 and 176 mg/L, respectively, and a 2-fold enhancement of product yield as compared to bioconversion with a single supply of α-pinene. The concentration of total conversion products in the culture medium reached 1.33 g/L [which corresponded product yield of 225 mg/(g dry cell L)]. This represents probably the most promising result reported to date for oxidative biotransformation of α-pinene by a wild-type microorganism.Electronic supplementary materialThe online version of this article (doi:10.1007/s10295-014-1550-0) contains supplementary material, which is available to authorized users.

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Stereoselective synthesis of a synthon for the A-ring of taxol from R-(+)-verbenone

Cited by 16 publications

References 24 publications

Monoterpenoids

Monoterpenoids

Kinetic study of α-pinene allylic oxidation over FePcCl16-NH2-SiO2 catalyst

Bioconversion of α-pinene by a novel cold-adapted fungusChrysosporium pannorum

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