The Pinene Path to Taxanes. 5. Stereocontrolled Synthesis of a Versatile Taxane Precursor

Wender, Paul A.; Badham, Neil F.; Conway, Simon P.; Floreancig, Paul E.; Glass, Timothy E.; Gränicher, Christian; Houze, Jonathan B.; Jänichen, Jan; Lee, Daesung; Marquess, Daniel G.; McGrane, Paul; Meng, Wei; Mucciaro, Thomas P.; Mühlebach, Michel; Natchus, Michael G.; Paulsen, Holger; Rawlins, David B.; Satkofsky, Jeffrey; Shuker, Anthony J.; Sutton, James; Taylor, Richard E.; Tomooka, Katsuhiko

doi:10.1021/ja9635387

Cited by 168 publications

(60 citation statements)

References 18 publications

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“…The above results are understandable in terms of the seemingly high reactivity of anion 17 towards traces of oxygen, perhaps by single electron transfer to form superoxide (O 2 .À ) and a fullerene radical. [23] Recombination and protonation give 18 a, which is not isolated under the conditions of the experiment. Loss of oxygen from 18 a or a similar peroxide by reduction affords 18 b.…”

Section: Preparation Of the No-ketene Acetalsmentioning

confidence: 93%

Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

et al. 1999

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Abstract:We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1 a ± e with C 60 proceeding through a tandem process to give the adducts 2 a ± e. The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electronrich N,O-ketene acetal moiety proceeds unusually fast at 25 8C, followed by an intramolecularly accelerated Diels ± Alder step that is highly diastereoselective. The structures of compounds 2 a ± e were determined from the 1 H and 13 C NMR shifts and from H ± H coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion ± radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.

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Section: Preparation Of the No-ketene Acetalsmentioning

confidence: 93%

Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

et al. 1999

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“…The next synthesis was reported by Danishefsky et al (1996;table abbreviation Da). Then Wender et al (1997a, 1997b; table abbreviations W-1 and W-2, respectively) reported another synthesis in two back-to-back communications, similar to Holton, Somoza, et al and Holton, Kim, et al Morihira et al (1998;table abbreviation Mo) published a communication followed by a full paper table abbreviation Ku). Between the publication of these two papers, another synthesis by Mukaiyama et al (1999; Nicolaou, Yang, et al (1994) and Mukaiyama et al (1999) papers, were published in the same journal.…”

Section: Example 4 (Cases 1 3 and 4)mentioning

confidence: 67%

“…The Holton, Somoza, et al paper is cited more often than the Holton, Kim, et al paper, while the Wender et al (1997a) paper has received about only half the number of citations of Wender et al (1997b). One may expect that the Holton, Kim, et al paper would receive more citations than Holton, Somoza, et al because the completion of the synthesis is reported in Holton, Kim, et al There is also a difference concerning citing journals.…”

Section: Example 4 (Cases 1 3 and 4)mentioning

confidence: 99%

“…One may expect that the Holton, Kim, et al paper would receive more citations than Holton, Somoza, et al because the completion of the synthesis is reported in Holton, Kim, et al There is also a difference concerning citing journals. The citation numbers for Wender et al (1997a) 1994 32 26 20 18 26 1995 84 77 70 62 84 1996 70 59 61 43 69 7 1997 57 67 46 44 57 21 6 15 17 1998 43 61 36 29 50 23 14 31 32 1999 32 51 30 22 33 21 16 21 22 12 11 2000 23 37 22 22 31 15 9 18 18 22 23 2 2001 19 31 8 13 16 8 5 10 12 6 17 9 Note. N-Na ϭ Nicolaou, Yang, et al (1994); N-AC ϭ Nicolaou, Dai, and Guy (1994) (2000) and Wender et al (1997b) in the Journal of Organic Chemistry are almost identical, while there is a strong tendency of authors of Tetrahedron Letters papers to cite Wender et al (1997b) instead of Wender et al (1997a) (see Table 6).…”

Section: Example 4 (Cases 1 3 and 4)mentioning

confidence: 99%

See 1 more Smart Citation

Comparative citation analysis of duplicate or highly related publications

Knothe¹

2006

J. Am. Soc. Inf. Sci.

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Four cases, illustrated by four examples, of duplicate or highly related publications can be distinguished and are analyzed here using citation data obtained from the Science Citation Index (SCI): (1) publication by different authors in the same journal; (2) the same author(s) publishing in different journals; (3) publication by different authors in different journals; (4) the same author(s) publishing highly related papers simultaneously in the same journal, often as part of a series of papers. Example 1, illustrating case 1, is an occurrence of highly related publications in mechanistic organic chemistry. Example 2, from analytical organic chemistry, contains elements of cases 2 and 3. Example 3, dealing solely with case 3, discusses two time-delayed publications from analytical biochemistry, which were highlighted by Garfield several times in the past to show how the SCI could be utilized to avoid duplicate publication. Example 4, derived from synthetic organic chemistry (total syntheses of taxol), contains elements of cases 1, 3, and 4 and, to a lesser extent, case 2. The citation records of the highly related or duplicate publications can deviate considerably from the journal impact factors; this was observed in three of the four examples relating to cases 2, 3, and 4. The examples suggest that citation of a paper may depend significantly on the journal in which it is published. As an indicator of this dependence, the journals in which the papers used in the present examples appeared were examined. Other factors such as key words in the paper title may also play a role.

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“…To date, seven methods was used in description the total synthesis of taxol [94][95][96][97][98][99][100][101][102][103]. Nicolaou and his co-workers were reported total synthesis of taxol and in 1994 [104][105][106][107].…”

Section: Oxetane As Building Blocks For Synthesis Of Taxolmentioning

confidence: 99%

Oxetanes as versatile building blocks in the total synthesis of natural products: An overview

Mahal

2015

Eur. J. Chem.

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The Pinene Path to Taxanes. 5. Stereocontrolled Synthesis of a Versatile Taxane Precursor

Cited by 168 publications

References 18 publications

Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

Comparative citation analysis of duplicate or highly related publications

Oxetanes as versatile building blocks in the total synthesis of natural products: An overview

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