The Structure of Strychnine. Formulation of the Neo Bases

Woodward, R. B.; Brehm, Warren J.

doi:10.1021/ja01186a034

Cited by 60 publications

(32 citation statements)

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“…In time, the neo -strychnine route was abandoned. Warren Brehm's research [ 2 ] had provided conclusive evidence for the Woodward structure ( 1 ). Synthesis plans were in full swing, and useful relay compounds were in demand.…”

Section: Discovering Natural Productsmentioning

confidence: 99%

Across Two Oceans onto the Reef—The Genesis of Marine Natural Products

Scheuer

2015

Culture of Chemistry

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Section: Discovering Natural Productsmentioning

confidence: 99%

Across Two Oceans onto the Reef—The Genesis of Marine Natural Products

Scheuer

2015

Culture of Chemistry

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“…Among Woodward's first notorious – and especially remembered today – structure determinations were of penicillin and strychnine . Their prominence was due to two factors.…”

Section: Woodward's Achievements In the Field Of Physical Organic Chementioning

confidence: 99%

“…Among Woodward's first notoriousand especially remembered todaystructure determinations were of penicillin [24] and strychnine. [25,26] Their prominence was due to two factors. First, these were important natural products, both with consequential scientific and medicinal history.…”

Section: The James Flack Norris Award In Physical Organic Chemistrymentioning

confidence: 99%

R. B. Woodward, A Great Physical Organic Chemist

Seeman

2014

J of Physical Organic Chem

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Robert Burns Woodward is considered one of the greatest synthetic organic chemists of our time, if not the greatest. This article presents evidence that Woodward was also one of the greatest physical organic chemists as well. Among Woodward and his collaborators' most important accomplishments in the field of physical organic chemistry are: the Woodward–Hoffmann rules; the derivation and use of structure–mechanism–reactivity relationships in his multifold structure determinations and total syntheses; the Woodward ultraviolet rules and the Octant Rule; and his early demonstration that synthetic organic chemistry can contribute to the synthesis of potential superconductors and thus, to material science. Copyright © 2014 John Wiley & Sons, Ltd.

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“…7), 43) and the structure was determined by Briggs and Robinson et al 44) and Woodward and Brehm. 45) The first total synthesis of (Ϫ)-strychnine was achieved by Woodward et al in 1954. 46) After that brilliant achievement, there were no other reports on the total synthesis of strychnine for about 40 years.…”

Section: Total Synthesis Of (؊)-Strychninementioning

confidence: 99%

Development of a Novel Synthetic Method for Ring Construction Using Organometallic Complexes and Its Application to the Total Syntheses of Natural Products

Mori

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Organometallic complexes are useful tools in synthetic organic chemistry. In particular, they play an important role in carbon-carbon bond formation. A metalacycle, i.e., a ring compound containing a transition metal, is a useful intermediate in synthetic organic chemistry. Oxidative cyclization of unsaturated hydrocarbons, such as alkene, alkyne, carbonyl compounds, or nitrile, using a low-valent transition metal is a useful reaction for synthesis of metalacycles. It is known that a metalacycle formed from a late transition metal and unsaturated hydrocarbons is not stable and is easily converted into the reductive elimination product or b-hydrogen elimination product (Eq. 1). Since the low-valent metal complex is regenerated in this reaction, the reaction proceeds with a catalytic amount of the transition metal. On the other hand, the metalacycle formed from an early transition metal and unsaturated hydrocarbons is fairly stable and can be converted into various compounds with functional groups by treatment with various agents (Eq. 2). Therefore a stoichiometric amount of the metal complex is required in this reaction.(1) (2) Negishi et al.2) and Nugent and Calabrese 3) reported the syntheses of zirconacycles 2 from diene, enyne, and diyne 1 using zirconocene (Cp 2 Zr). Hydrolysis of zirconacycle afforded the cyclized compound 3 (Chart 1).Negishi et al. also found a synthetic method of dibutylzirconocene (Cp 2 ZrBu 2 ) from zirconocenedichloride (Cp 2 ZrCl 2 ) and butyl lithium, and dibutylzirconocene is easily converted into zirconocene coordinated by a butene ligand in situ at room temperature 4) (Eq. 3).This was a great discovery in zirconium chemistry because it is difficult to isolate zirconocene with no ligand. We were interested in those results and attempted to form carbon-carbon bonds between the unsaturated hydrocarbons, such as enyne and diene, using zirconocene. Synthesis of Heterocycles Using Zirconium-Mediated Cyclization and Total Synthesis of (؊)-DendrobineThe zirconacycles 2 were easily synthesized in situ from Cp 2 ZrCl 2 and diene, enyne, or diyne 1. To a THF solution of Cp 2 ZrCl 2 and unsaturated hydrocarbon 1 was added BuLi at Ϫ78°C under argon gas, and the solution was stirred at room Organometallic complexes are useful tools in synthetic organic chemistry. We investigated a novel synthetic method for ring construction using organometallic complexes and synthesized natural products and biologically active substances using these methods. Metalacycles formed from an early transition metal and diene, enyne, and diyne are stable under the reaction conditions and they are easily converted into compounds with functional groups by the addition of various agents. We have developed a novel synthetic method of heterocycles from enyne and diene using Cp 2 ZrBu 2 . The total syntheses of (؊)-dendrobine, (؎)-mecembrane, and (؎)-mecembrine were achieved using this procedure. To synthesize these natural products as a chiral form, a novel palladium-catalyzed asymmetric allylic amination was developed, an...

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The Structure of Strychnine. Formulation of the Neo Bases

Cited by 60 publications

References 1 publication

Across Two Oceans onto the Reef—The Genesis of Marine Natural Products

Across Two Oceans onto the Reef—The Genesis of Marine Natural Products

R. B. Woodward, A Great Physical Organic Chemist

Development of a Novel Synthetic Method for Ring Construction Using Organometallic Complexes and Its Application to the Total Syntheses of Natural Products

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