Total Synthesis of (±)-Cermizine B

Shi, Xin; Deng, Zhen-Tao; Zhu, Yu; Bao, Ying; Shao, Li; Zhao, Qin‐Shi

doi:10.1021/acs.joc.7b02073

Cited by 10 publications

(12 citation statements)

References 42 publications

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“…To avoid destroying the carbonyl group during the Pt-catalysed hydrogenation, the carbonyl group of 1 was protected using ethylene glycol/PTSA. Then, the PtO 2 -catalysed hydrogenation was performed steadily, followed by work-up with HCl to form an iminium intermediate 6, which was subsequently trapped by the hydrogen anion using NaBH 4 , 10,33 to give (±)-cermizine D (9) in 20% yield. With the Weinreb amide 3 in hand, we obtained the known intermediate 11 resulting from the substitution by the methyllithium reagent in 90% yield.…”

Section: Resultsmentioning

confidence: 99%

“…1). [5][6][7][8][9][10][11][12] Although cermizine C has been the topic of numerous synthetic papers, 7,8,[13][14][15][16][17][18][19][20][21][22] to date there have been only three total syntheses of cermizine D. 20,[23][24][25] In 2008, Takayama and co-workers reported the first asymmetric total synthesis of (+)cermizine D, which consisted of an 18-step route featuring an oxazolidinone intermediate as a key cyclisation precursor. 20,23 In 2012, a second synthesis of (+)-cermizine D was published by Carter and collaborators, which included two different approaches, a nine-step cuprate addition strategy and a PhSCH 2 I alkylation pathway in 16 steps overall.…”

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confidence: 99%

“…In our previous work we proved that introducing a pyridine group via conjugate addition of the metalated 2-picoline was more direct and more effective. 10 To make use of 2-picoline in other lycopodium alkaloids, herein we describe a total synthesis of (±)-cermizine D through the orderly combination of commercial methyl crotonate and metalated 2-picoline. In addition, we report the formal synthesis of (±)-cermizine C.…”

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A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

Shi

Bao

Deng

et al. 2018

Journal of Chemical Research

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A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C were achieved. The four-step total synthesis comprised mainly a Michael addition, a Weinreb amide-activated substitution and a sequence of ketalation/PtO2-catalysed dearomatisation/reductive amination reactions that resulted in ring closure in 13.7% overall yield. The formal synthesis was accomplished in 29.7% overall yield.

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A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

Shi

Bao

Deng

et al. 2018

Journal of Chemical Research

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“…In 2017, Zhao group reported another total synthesis of (�)-cermizine B (2) via reaction of methyl 4-methyl-6-oxocyclohex-1-ene-1-carboxylate (13), 2-picoline (14) and acrolein (15) (Scheme 2). [15] According to the mechanism nine-step synthesis of this heterocyclic scaffold includes two uninterrupted Michael additions, Krapcho decarboxylation, double reductive amination. Acrolein 15is involved in the double Michael cascade reaction under catalytic amount of Bu 4 NF and is a carbon source in the construction of the alkaloid core.…”

Section: Lycopodium Alkaloidsmentioning

confidence: 99%

Recent Advances in Total Synthesis of Alkaloids from α,β‐Unsaturated Aldehydes

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Verochkina

2020

ChemistrySelect

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Alkaloids are structurally complex pharmacologically valuable natural products, the synthesis of which attracts the attention of the world scientific community. This review summarizes and highlights the recent advancements in the total synthesis of different family alkaloids (such as Lycopodium, Manzamine, Indole, Amaryllidaceae, as well as other alkaloids) from transformations of α,β‐unsaturated aldehydes.

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“…DASA can be implemented in different experimental setups such as QED [42], coupled waveguides [43], acoustics [44,45], and electronics [46]. For example an optical system composed of two coupled waveguides [48] can be used to experimentally demonstrate our proposal where each waveguide has two segments.…”

Section: Pacs Numbersmentioning

confidence: 99%

Eigenstates Transition without Undergoing an Adiabatic Process

2019

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We introduce a class of non-Hermitian Hamiltonians that offers a dynamical approach to shortcut to adiabaticity (DASA). In particular, in our proposed 2 × 2 Hamiltonians, one eigenvalue is absolutely real and the other one is complex. This specific form of the eigenvalues helps us to exponentially decay the population in an undesired eigenfunction or amplify the population in the desired state while keeping the probability amplitude in the other eigenfunction conserved. This provides us with a powerful method to have a diabatic process with the same outcome as its corresponding adiabatic process. In contrast to standard shortcuts to adiabaticity, our Hamiltonians have a much simpler form with a lower thermodynamic cost. Furthermore, we show that DASA can be extended to higher dimensions using the parameters associated with our 2 × 2 Hamiltonians. Our proposed Hamiltonians not only have application in DASA but also can be used for tunable mode selection and filtering in acoustics, electronics, and optics. PACS numbers:The current transition of technological advancements from classical to quantum systems, makes the quantum adiabatic theorem an important matter beyond a conceptual curiosity with widespread applications in atomic and molecular physics [1][2][3][4][5][6], quantum Hall physics [7,8], the physics of geometric phase [9], quantum computation [10-12], quantum annealing [13][14][15], and quantum simulations [16]. The adiabatic theorem in its earliest form [17] states that a quantum system with a timedependent Hamiltonian H( t) and non-degenerate discrete states will remain in its instantaneous ground state (GS) if it is initially prepared in its GS and its Hamiltonian changes sufficiently slow in time, namely → 0. Apart from some inconsistency for certain Hamiltonians [18][19][20], while there is no doubt about the correctness of adiabatic theorem, in practice it is very difficult, if not impossible, to satisfy its necessary conditions due to the competition between the scan time and decoherence time resulted from the existence and unavoidable undesired non-adiabatic channels. To overcome this problem and improve the population transfer from the GS of the original system to the GS of the final system [21] without disturbing other states some techniques have been proposed including nonlinear level crossing [22], amplitudemodulated and composite pulses [23,24], and parallel adiabatic passage [25]. Another growing approach is the so-called "shortcuts to adiabaticity" where one looks for fast processes with the same outcome as an ideal and yet infinitely slow process. The common approach in the shortcuts to adiabaticity is to nullify the non-adiabatic coupling by introducing the so-called counter-diabatic extra field [26][27][28][29][30]. The shortcut to adiabaticity originally studied in Hermitian systems and has been extended to non-Hermitian systems [31][32][33]. The rapid adiabatic passage in the above methods comes with a fundamental problem, namely the cost of increasing the coupling in the Hermitian case...

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Total Synthesis of (±)-Cermizine B

Cited by 10 publications

References 42 publications

A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

Recent Advances in Total Synthesis of Alkaloids from α,β‐Unsaturated Aldehydes

Eigenstates Transition without Undergoing an Adiabatic Process

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