Enantioselective Total Synthesis of the Diterpenes Kempene‐2, Kempene‐1, and 3‐<i>epi</i>‐Kempene‐1 from the Defense Secretion of Higher Termites

Schubert, Melanie; Metz, Peter

doi:10.1002/anie.201007551

Cited by 38 publications

(17 citation statements)

References 33 publications

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“…[158] Two-fold ene-yne metathesis, pioneered by the group of Grubbs in the 1990s, [159] has also proven to be an efficient strategy for the synthesis of structures containing up to four new rings. [160,161] Some of the most recent examples feature in the work reported by the groups of Yang, [162] Fukuyama, [163] Metz, [164] Oguri, [165] Movassaghi, [166] Mulzer, [167] and Lee. [168] Olefin metathesis steps have also been combined with other transformations in independent reaction sequences.…”

Section: Independent Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Section: Independent Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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“…Recently, Metz has explored the application of a domino metathetic strategy to access the natural compounds highlighted in Scheme 19 in an enantioselective fashion. 56,57 Scheme 19 Application of dienyne RCM to the enantioselective synthesis of kempene-2, hydroxykempenone and other naturally occurring kempanes…”

Section: Scheme 17 Preparation Of Taxol-type Carbocyclic Systems Via mentioning

confidence: 99%

Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Bernardi

Colombo²,

Serra³

2020

Synthesis

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Enyne metathesis reactions are powerful tools for the preparation of a wide range of synthetic and natural chemical substances with increasing efficiency and environmental sustainability. The driving force of the reaction is the formation of a stable conjugated system, i.e., a diene, which through further functionalization steps can be used for the construction of skeletally complex molecular architectures. These concepts are exploited to design cascade reaction sequences, where multiple rings can be formed in a one-pot fashion by combining metathetic protocols with various chemical transformations. The strong correlation between synthetic organic chemistry and medicinal chemistry prompted us to review the most notable approaches for the synthesis of biologically relevant compounds via enyne metathesis-based one-pot processes. With the aim to provide a modern and practical overview, by taking into consideration the scientific literature on this topic, we have focused the majority of our attention on the research performed in the last decade. This review covers the literature from 2003 to 2020.1 Introduction2 Ethylene-Mediated Processes3 RCEYM/CM and CEYM/RCM Processes4 Enyne Metathesis/Diels–Alder-Based Processes5 RCM of Dienynes6 RCM of Tethered Dienynes7 Relay Metathesis8 Ring-Rearrangement Metathesis9 RCEYM/Transition-Metal-Catalyzed C–C Bond-Forming Processes10 Conclusions11 List of Acronyms

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“…al. [82]. The starting dienynes were obtained in a high enantiomeric purity starting form 2,6-dimethyl-1,4-benzoquinone and isoprene via an asymmetric Diels-Alder reaction.…”

Section: Kempene Diterpenesmentioning

confidence: 99%

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

Drăguţan¹,

Drăguţan²,

Demonceau³

et al. 2020

Beilstein J. Org. Chem.

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This account surveys the current progress on the application of intra- and intermolecular enyne metathesis as main key steps in the synthesis of challenging structural motifs and stereochemistries found in bioactive compounds. Special emphasis is placed on ruthenium catalysts as promoters of enyne metathesis to build the desired 1,3-dienic units. The advantageous association of this approach with name reactions like Grignard, Wittig, Diels–Alder, Suzuki–Miyaura, Heck cross-coupling, etc. is illustrated. Examples unveil the generality of such tandem reactions in providing not only the intricate structures of known, in vivo effective substances but also for designing chemically modified analogs as valid alternatives for further therapeutic agents.

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Enantioselective Total Synthesis of the Diterpenes Kempene‐2, Kempene‐1, and 3‐epi‐Kempene‐1 from the Defense Secretion of Higher Termites

Cited by 38 publications

References 33 publications

Multi-Bond Forming Processes in Efficient Synthesis

Multi-Bond Forming Processes in Efficient Synthesis

Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

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