Synthetic studies on the seven- and eight-membered rings by the intramolecular Nozaki–Hiyama reaction of the allylic phosphates

Iwamoto, Mitsuhiro; Miyano, Masayuki; Utsugi, Masayuki; Kawada, Hatsuo; Nakada, Masahisa

doi:10.1016/j.tetlet.2004.09.142

Cited by 15 publications

(3 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Strategies and Lessons Learned from this Synthesis. In 2004, Nakada and co-workers 103 developed an intramolecular Nozaki−Hiyama allylation of allylic phosphate for construction of eight-membered rings of Taxol (Scheme 17A).…”

Section: Nakada's Formal Synthesis Of Taxol (2015)mentioning

confidence: 99%

“…Nakada and co-workers − reported a series of synthetic studies toward Taxol since 1998, and culminated in a formal synthesis of Taxol using a convergent strategy in 2015 (Figure ). , Remarkable features of this synthesis were as follows: (i) a 1,2-addition to connect A and C rings at the C1–C2 site; (ii) a Pd-catalyzed alkenylation to install the B ring by C10–C11 bond formation; and (iii) the oxetane D ring was constructed by a well-established S N 2 cyclization.…”

Section: Synthesis Based On Forming the C10–c11 Bondmentioning

confidence: 99%

“…In 2004, Nakada and co-workers developed an intramolecular Nozaki–Hiyama allylation of allylic phosphate for construction of eight-membered rings of Taxol (Scheme A). The precursor 119 was treated with CrCl 2 -LiI; however, only 15% yield of cyclized product 120 was obtained, and the major product was the protonated adduct of 119 .…”

Section: Synthesis Based On Forming the C10–c11 Bondmentioning

confidence: 99%

See 2 more Smart Citations

Strategies and Lessons Learned from Total Synthesis of Taxol

et al. 2023

View full text Add to dashboard Cite

Taxol (paclitaxel), the most well-known taxane diterpenoid, is the best-selling natural-source anticancer drug ever produced and one of the most common prescriptions in the treatment of breast, lung, and ovarian cancers, saving countless lives around the world. Structurally, Taxol possesses a highly oxygenated [6−8−6−4] core bearing 11 stereocenters, seven of which are contiguous chiral centers. Moreover, the extremely strained bicyclo[5.3.1] undecane ring system with a bridgehead double bond is a unique structural feature. All these features make Taxol a highly challenging synthetic target. Tremendous synthetic efforts from more than 60 research groups around the world have already culminated in ten total syntheses and three formal syntheses, as well as more than 60 synthetic model studies of Taxol. This review is intended to provide a long-overdue appraisal of the great achievements in the total syntheses of Taxol reported in the last few decades. In doing so, we summarize the development of synthesis toward Taxol from 1994 to 2022, including the evolution of synthetic strategy for accessing this complex molecular scaffold and key lessons learned from such endeavors. Finally, we briefly discuss the future of the research in this area.

show abstract

Section: Nakada's Formal Synthesis Of Taxol (2015)mentioning

confidence: 99%

Section: Synthesis Based On Forming the C10–c11 Bondmentioning

confidence: 99%

Section: Synthesis Based On Forming the C10–c11 Bondmentioning

confidence: 99%

See 1 more Smart Citation

Strategies and Lessons Learned from Total Synthesis of Taxol

et al. 2023

View full text Add to dashboard Cite

show abstract

Pivaloyloxymethyl Iodide

Butler¹

2008

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Nozaki‐Hiyama‐Kishi Reaction

Kallemeyn¹

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

The chromium‐promoted coupling between a halide and a carbonyl compound is often known as the Nozaki–Hiyama–Kishi reaction. An intramolecular version of this reaction to afford a cyclic product is generally called the Nozaki–Hiyama–Kishi cyclization. Overall special features and weaknesses of this reaction have been discussed. It has been reported that when a bromofluoroalkene is applied as the nucleophile, only ( E )‐bromofluoroalkene couples with the aldehyde, giving moderate to good yields. When γ‐monosubstituted allylhalides are used as the nucleophiles, the corresponding homoallyl alcohols form with an excellent anti selectivity, regardless of the original configuration of the allyl halides. Other catalytic conditions and uses of chiral ligands have been discussed for this reaction. This reaction is useful for the synthesis of the natural products.

show abstract

Synthetic studies on the seven- and eight-membered rings by the intramolecular Nozaki–Hiyama reaction of the allylic phosphates

Cited by 15 publications

References 22 publications

Strategies and Lessons Learned from Total Synthesis of Taxol

Strategies and Lessons Learned from Total Synthesis of Taxol

Pivaloyloxymethyl Iodide

Nozaki‐Hiyama‐Kishi Reaction

Contact Info

Product

Resources

About