Total Synthesis of <i>d,l</i>-Caryophyllene and <i>d,l</i>-Isocaryophyllene

Corey, E. J.; Mitra, R. B.; Uda, Hisashi

doi:10.1021/ja01057a040

Cited by 231 publications

(55 citation statements)

References 1 publication

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“…All sesquiterpene synthases transform the structurally relatively simple substrate E,E-farnesyl diphosphate (FDP, C 15 unit) into various sesquiterpenes including macrocyclic, bicyclic and tricyclic compounds [4]. The complex C 15 -carbon backbones of sesquiterpenes combined with their limited number of functional groups make it difficult to produce substances such as patchoulol or trans-β-caryophyllene by organic synthesis approaches [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Characterisation of a Recombinant Patchoulol Synthase Variant for Biocatalytic Production of Terpenes

Frister

Hartwig

Alemdar

et al. 2015

Appl Biochem Biotechnol

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The patchoulol synthase (PTS) is a multi-product sesquiterpene synthases which is the central enzyme for biosynthesis of patchouli essential oil in the patchouli plant. Sesquiterpene synthases catalyse the formation of various complex carbon backbones difficult to approach by organic synthesis. Here, we report the characterisation of a recombinant patchoulol synthase complementary DNA (cDNA) variant (PTS var. 1), exhibiting significant amino acid exchanges compared to the native PTS. The product spectrum using the natural substrate E,E-farnesyl diphosphate (FDP) as well as terpenoid products resulting from conversions employing alternative substrates was analysed by GC-MS. In respect to a potential use as a biocatalyst, important enzymatic parameters such as the optimal reaction conditions, kinetic behaviour and the product selectivity were studied as well. Adjusting the reaction conditions, an increased patchoulol ratio in the recombinant essential oil was achieved. Nevertheless, the ratio remained lower than in plant-derived patchouli oil. As alternative substrates, several prenyl diposphates were accepted and converted in numerous compounds by the PTS var. 1, revealing its great biocatalytic potential.

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Section: Introductionmentioning

confidence: 99%

Characterisation of a Recombinant Patchoulol Synthase Variant for Biocatalytic Production of Terpenes

Frister

Hartwig

Alemdar

et al. 2015

Appl Biochem Biotechnol

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“…In 1963, Corey published a synthesis of the sesquiterpenes caryophyllene and isocaryophyllene, [40,41] one of the classics in the area of terpene synthesis. The key step in the preparation of these sesquiterpenes is a Grob fragmentation of a 5/6/4-fused ring intermediate in order to establish the nine-membered ring present in caryophyllene (106) and isocaryophyllene (109).…”

Section: Caryophyllene Corey 1963mentioning

confidence: 99%

Synthesis of Protoilludanes and Related Sesquiterpenes

2011

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Natural products continue to hold the interest and attention of a wide chemical community. This is due to their biological properties and potential applicability in health care and plant protection, as well as their frequently complex molecular architectures and arrays of functionality, which make them a challenge for total synthesis and a testing ground for novel methodology. These criteria are met to an extraordinary degree by protoilludanes, which are sesquiterpenes with a characteristic tricyclic 5/6/4‐framework. The fortieth anniversary of the first protoilludane synthesis has now been taken as an occasion to review the main aspects of this fascinating class of compounds. Biosynthesis, biological properties and the unusually rich variety of synthetic approaches developed over the past forty years are discussed. About 80 different substitution patterns and 15 completed or uncompleted synthetic routes are listed in this review with the goal of providing a multifacetted picture of the changes in and development of synthetic philosophy and methodology from past to present.

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“…7 The ring junction stereochemistry, the strained four-membered ring and the non-trivial nine-membered ring with the correct double bond geometry were all achieved by careful choice of the synthetic route (Scheme 7.1). 8 The four-membered ring was constructed in one step using a [2 þ 2] photochemically mediated reaction between cyclohexenone and excess isobutene which gave the desired regiochemistry in the cis-fused cyclohexanone 2.…”

Section: Overcoming Challenges In the Small-scale Synthesismentioning

confidence: 99%

Challenges in the Synthesis of Natural and Non‐Natural Volatiles

Birkbeck¹

2010

The Chemistry and Biology of Volatiles

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Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene

Cited by 231 publications

References 1 publication

Characterisation of a Recombinant Patchoulol Synthase Variant for Biocatalytic Production of Terpenes

Characterisation of a Recombinant Patchoulol Synthase Variant for Biocatalytic Production of Terpenes

Synthesis of Protoilludanes and Related Sesquiterpenes

Challenges in the Synthesis of Natural and Non‐Natural Volatiles

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