Synthetic Study toward Total Synthesis of (±)-Germine: Synthesis of (±)-4-Methylenegermine

Stork, Gilbert; Yamashita, Ayako; Hanson, Robert M.; Phan, Ly T.; Phillips, E. O.; Dubé, Daniel; Bos, Pieter H.; Clark, Andrew J.; Gough, M. J.; Greenlee, Mark L.; Jiang, Yimin; Jones, Keith; Kitamura, Masato; Leonard, John; Liu, Tongzhu; Parsons, Philip J.; Venkatesan, Aranapakam M.

doi:10.1021/acs.orglett.7b02434

Cited by 17 publications

(14 citation statements)

References 27 publications

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“…The reaction leads to the selective formation of four stereocenters with high exo/endo-and facialselectivities. 51 Scheme 31 Stereoselective, bis-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfide-mediated Diels-Alder step in the total synthesis of (±)-4methylenegermine.…”

Section: Total Synthesis Of (±)-4-methylenegerminementioning

confidence: 99%

“…The total synthesis of (±)-4-methylenegermine was reported through a remarkable and highly stereoselective Diels-Alder cycloaddition (Scheme 31). 50,51 By way of a bis-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfide mediated transformation, which acts as a radical inhibitor, the coupling between precursor 112 and the pyridine-derived enone 113 was successfully carried out. The reaction leads…”

Section: Total Synthesis Of (±)-4-methylenegerminementioning

confidence: 99%

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Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

et al. 2021

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The Diels-Alder reaction has long established its high rank in the toolbox of any natural product chemist. The tremendous toleration of building blocks of various complexity and derivatization degree, as well as the enablement of furnishing six-membered rings with well-defined stereochemistry represents its main features and advantages. In recent years, many total syntheses of natural products relied at some point on the use of a [4+2]-cycloaddition step. Among classic approaches, several modifications of the Diels-Alder reaction, such as hetero-Diels-Alder reactions, dehydro-Diels-Alder reactions or domino-Diels-Alder reactions have been employed to extend the scope in the synthesis of natural products. Our review covers the application of the Diels-Alder reaction in natural product syntheses from 2017 to 2020, as well as selected methodologies which were inspired by, or could be used to access natural products.

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Section: Total Synthesis Of (±)-4-methylenegerminementioning

confidence: 99%

Section: Total Synthesis Of (±)-4-methylenegerminementioning

confidence: 99%

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

et al. 2021

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“…9 In Gilbert Stork's last paper, published shortly before he died in 2017, a complicated Diels-Alder reaction was used to create a cyclohexene with complete control of stereochemistry, both exo/endo and facial selectivity ( Figure 5B), leading to four new stereocenters, properly fixed with respect to the pre-existing stereocenters in the diene. 10 Other types of pericyclic reaction are also commonly used in synthesis, such as the Ireland-Claisen rearrangement. Figure 6 shows this [3,3]-sigmatropic shift used in Rizzacasa's (+)zaragozic acid C synthesis from Zakarian's review on the use of these reactions in synthesis 11 and an electrocyclization used in Kwon's approach to the synthesis of reserpine, 12 respectively.…”

Section: Synthetically Useful Pericyclic Reactionsmentioning

confidence: 99%

The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery

et al. 2019

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“…I met Gilbert for the last time on April 11, 2018, when he had just submitted his last publication. 7,8 Organic chemistry at Columbia was extremely strong in research and education. Every Thursday evening after dinner, we had an organic seminar/problem session where all organic professors, Stork, Breslow, Nakanishi, Katz, Turro and Still, sat in the front row of a classroom in the Havemeyer Hall and gave insightful comments for students and postdocs.…”

Section: Total Synthesis Of Cytochalasins 1978 1980mentioning

confidence: 99%

Chemistry: A Bridge between Molecular World and Real World

Nakamura

2018

J. Synth. Org. Chem. Jpn.

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This essay summarizes a personal history of studies on uoride mediated reactions of enol silyl ethers, metal homoenolate, cytochalasin and cortisone synthesis, cycloaddition chemistry of cyclopropenone acetals and dipolar trimethylenemethanes, biological activity of organofullerenes and DNA and siRNA delivery, organocuprate(I) reaction mechanisms, iron catalyzed cross coupling and C H activation reactions, 15 O labeling for positron emission tomography (PET), functional fullerene molecules including bucky ferrocene, shuttlecock molecules and [10]cyclophenacene, fullerene bilayer vesicles, new design materials for organic and lead perovskite solar cell fabrication, carbon bridged oligophenylene vinylenes and single molecule atomic resolution real time transmission electron microscopy (SMART EM) for structural and kinetic studies of molecules and molecular clusters. It also describes how the encounters with key people may change the course of your scienti c research as well as of your personal life. These examples suggest that life is a stochastic process, and, moreover, science in the future would be something that we do not even imagine now as a subject of research. Figure 2. Prof. Mukaiyama at an alumni party around 1980.

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Synthetic Study toward Total Synthesis of (±)-Germine: Synthesis of (±)-4-Methylenegermine

Abstract: The total synthesis of 4-methylenegermine is described

Cited by 17 publications

References 27 publications

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery

Chemistry: A Bridge between Molecular World and Real World

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