Investigations of the intramolecular Ni(II)/Cr(II)-mediated coupling reaction: Application to the taxane ring system

Kress, Michael H.; Ruel, Réjean; Miller, William H.; Kishi, Yoshito

doi:10.1016/s0040-4039(00)61712-4

Cited by 35 publications

(21 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The choice of fragment 7 poses the additional opportunity to investigate the influence of the protecting groups at C3 and C4 (cyclic or acyclic) on the stereochemical outcome of the Nozaki-Hiyama-Kishi cyclization. The different local conformations that might be enforced by the protecting groups at C3 and C4 were expected to impart changes on the geometry of the transition state as proposed by Kishi 13 and Schreiber 14 .…”

Section: Introductionmentioning

confidence: 94%

“…The remaining reagents were purchased from commercial suppliers and used without further purification. 1 H NMR spectra were recorded at 300 or 500 MHz; 13 C NMR spectra were recorded at 75 or 125 MHz. Residual CHCl 3 (d 7.26) was used as an internal standart in 1 H NMR spectra.…”

Section: Generalmentioning

confidence: 99%

“…Residual CHCl 3 (d 7.26) was used as an internal standart in 1 H NMR spectra. 13 C NMR spectra were referenced to CDCl 3 at d 77.0. Optical rotations were measured at 25 o C in a Polamat A (Carl Zeiss) polarimeter at 546 nm (mercury line).…”

Section: Generalmentioning

confidence: 99%

See 2 more Smart Citations

The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D

Pilli¹,

Victor²

2001

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

O uso da reação de Nozaki-Hiyama-Kishi para a formação de lactonas de 10 membros é descrita. A influência dos grupos de proteção em C4 e C5 sobre a estereoquímica do novo centro estereogênico formado em C7 foi investigada. A utilidade desta metodologia ficou demonstrada com a síntese total e estereosseletiva da (-)-decarestrictina D a partir do 1,3-propanodiol e poliidroxibutirato (PHB) em 13 etapas e 6,3% de rendimento total. The use of the intramolecular Nozaki-Hiyama-Kishi reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C4 and C5 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. The utility of this methodology has been demonstrated in the stereoselective total synthesis of (-)-decarestrictine D from 1,3-propanediol and polyhydroxybutyrate (PHB) in 13 steps and 6.3% overall yield.

show abstract

Section: Introductionmentioning

confidence: 94%

Section: Generalmentioning

confidence: 99%

See 1 more Smart Citation

The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D

Pilli¹,

Victor²

2001

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Whereas 2 has been chemically constructed by 10 research groups, the total synthesis of 1 was only reported in a dissertation from Kishi's group in 1998 . In this report, Ni II /Cr II ‐mediated coupling was applied for the construction of the eight‐membered B‐ring and 1 was synthesized in 38 steps (longest linear sequence). Herein, we describe a new radical‐based strategy for the total synthesis of 1 .…”

Section: Methodsmentioning

confidence: 99%

“…Thepresence of two quaternary carbon centers (C8, C15) and two olefins (C4, C11) in this densely oxygenated skeleton further heightens the synthetic challenge of 1.Whereas 2 has been chemically constructed by 10 research groups, [5,6] the totals ynthesis of 1 was only reported in ad issertation from Kishisg roup in 1998. [7] In this report, Ni II /Cr II -mediated coupling [8] was applied for the construction of the eightmembered B-ring and 1 was synthesized in 38 steps (longest linear sequence). Herein, we describe an ew radical-based strategy for the total synthesis of 1.Acombination of intermolecular and intramolecular radical coupling reactions permitted us to efficiently annulate the B-ring from A-and Cring fragments.…”

mentioning

confidence: 99%

Total Synthesis of 1‐Hydroxytaxinine

et al. 2019

View full text Add to dashboard Cite

1-Hydroxytaxinine (1)isacytotoxic taxane diterpenoid. Its central eight-membered B-ring possesses four oxygenfunctionalizedc enters (C1, C2, C9, and C10) and two quaternary carbon centers (C8 and C15), and is fused with six-membered A-and C-rings.The densely functionalizedand intricately fused structure of 1 makes it ah ighly challenging synthetic target. Reported here is an efficient radical-based strategy for assembling 1 from A-and C-ring fragments.T he A-ring bearing an a-alkoxyacyl telluride moiety underwent intermolecular coupling with the C-ring fragment by aE t 3 B/ O 2 -promoted decarbonylative radical formation. After construction of the C8-quaternary stereocenter,apinacol coupling reaction using alow-valent titanium reagent formed the B-ring with stereoselective installation of the C1,C2-diol. Subsequent manipulations at the A-and C-rings furnished 1 in 26 total steps.

show abstract

Addition of Organochromium Reagents to Carbonyl Compounds

Takai

2004

Organic Reactions

View full text Add to dashboard Cite

Organochromium compounds can be prepared by two methods: (1) transmetallation from the corresponding organolithium, ‐magnesium, or –zinc compounds with chromium(III) halides, and (2) reduction of organic substrates, such as halides and unsaturated compounds with chromium(II) salts. The second method is usually the one ised because the first method suffers from low solubility of chromium(III) salts in ethereal solvents and from the difficulty of preparing organolithium compounds. Low‐valent chromium species are reducing agents. Reduction of various types of organic halides and compounds having unsaturated hetero‐hetero bonds with the chromium (II) species is discussed. Also described are the transmetallation to organochromium compounds from other organometallics, the nature of the carbon‐chromium bonds, and the X‐ray structure of chromium compounds. Reactions of organochromium reagents with carbonyl compounds and their scope and limitations are described. Included in this discussion are the geminal chromium reagents. Other reagents discussed are the chromium‐nickel compounds and alkylchromium and other organochromium reagents.

show abstract

Investigations of the intramolecular Ni(II)/Cr(II)-mediated coupling reaction: Application to the taxane ring system

Cited by 35 publications

References 3 publications

The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D

The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D

Total Synthesis of 1‐Hydroxytaxinine

Addition of Organochromium Reagents to Carbonyl Compounds

Contact Info

Product

Resources

About