Výsledky vyhledávání - "Robert Daeffler"

A Study of the Paterson Boron Aldol Reaction as Used in the Large-Scale Total Synthesis of the Anticancer Marine Natural Product (+)-Discodermolide

Autor: Robert Daeffler, Stuart J. Mickel, Walter Prikoszovich

Publikováno v: Organic Process Research & Development. 9:113-120

This note discusses an optimisation study of a key reagent-controlled enantioselective boron enolate aldol reaction forming the C6−C7 bond and the C7 hydroxyl-bearing stereocenter in (+)-discodermolide. Conditions were found which increased the yie

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::f05e8bc062d372d78af188a0e8d145ad
https://doi.org/10.1021/op049800a

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Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 5: Linkage of Fragments C1-6 and C7-24 and Finale

Autor: Frederick Ray Kinder, Robert Daeffler, Ernst Kuesters, Weichun Chen, Emil Schmid, Run-Ming Wang, Daniel Niederer, Kapa Prasad, Remo Gamboni, Karl Schaer, Ian Paterson, Isabelle Lyothier, Adnan Osmani, Stuart J. Mickel, Kurt Königsberger, Gordon J. Florence, Loeser Eric M, Oljan Repic, Timothy Michael Ramsey

Publikováno v: Organic Process Research & Development. 8:122-130

The finale of the large-scale preparation of 60 g of the highly complex marine natural product, (+)-discodermolide (1), using a hybridized Novartis−Smith−Paterson synthetic route is presented. This contribution, which is the concluding part of a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::38fae1061260aceaea14fa8b5fb7d4a9
https://doi.org/10.1021/op034134j

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Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2: Synthesis of Fragments C1-6 and C9-14

Publikováno v: Organic Process Research & Development. 8:101-106

Kilogram-scale syntheses of fragments C1-6 (6) and C9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation of byproducts that

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::8d48749d744ab1158633990c308bc966
https://doi.org/10.1021/op0341317

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Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1: Synthetic Strategy and Preparation of a Common Precursor

Publikováno v: Organic Process Research & Development. 8:92-100

The synthetic strategy for producing multigram quantities of (+)-discodermolide (1) using a hybridized Novartis−Smith−Paterson synthetic route via common precursor 3 is described. In the first part of this five-part series, we present a multikilo

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::cc6724fb15e2f2f3403c7b2f36e2a0a7
https://doi.org/10.1021/op034130e

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Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 4: Preparation of Fragment C7-24

Publikováno v: Organic Process Research & Development. 8:113-121

Coupling of C9-14 (4) and C15-21 (5a) fragments to produce the cis-trisubstituted olefin was achieved using Suzuki-type coupling conditions employed by Marshall (5a/tert-BuLi/B-OMe-9-BBN added to 4/Cs2CO3/Pd(dppf)2). The terminal (Z)-diene moiety was

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::636e79cabb468b439dd0390f88424064
https://doi.org/10.1021/op034133r

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Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 3: Synthesis of Fragment C15-21

Publikováno v: Organic Process Research & Development. 8:107-112

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::e4deba2b204b70a064f31171b46749dc
https://doi.org/10.1021/op034132z

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Large-Scale Synthesis of the anti-Cancer Marine Natural Product (+)-Discodermolide. Part 5. Linkage of Fragments C1-6 and C7-24 and Finale

Autor: Adnan Osmani, Karl Schaer, Ernst Kuesters, Emil Schmid, Robert Daeffler, Daniel Niederer, Stuart J. Mickel, Remo Gamboni

Publikováno v: ChemInform. 35

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::b4c93996044d070418f01f390590b199
https://doi.org/10.1002/chin.200424191

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Large-Scale Synthesis of the anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1. Synthetic Strategy and Preparation of a Common Precursor (I)

Autor: Stuart J. Mickel, Daniel Niederer, Robert Daeffler, Remo Gamboni, Karl Schaer, Brigitte Berod, Manuela Seeger-Weibel, Klaus Schreiner, Adnan Osmani, Gottfried Sedelmeier

Publikováno v: ChemInform. 35

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::a6abfccfd573edef9907ad66ca0b0135
https://doi.org/10.1002/chin.200424188

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Synthetic analogues of the microtubule-stabilizing agent (+)-discodermolide: preparation and biological activity

Autor: Sarath P. Gunasekera, Stuart J. Mickel, Robert Daeffler, Daniel Niederer, Amy E. Wright, Patricia Linley, Tara Pitts

Publikováno v: Journal of natural products. 67(5)

A series of seven synthetic discodermolide analogues 2-8, which are minor side products generated during the final stages in the synthesis of (+)-discodermolide (1), have been purified and evaluated for in vitro cytotoxicity against A549, P388, MFC-7

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ab172104bab873184e554ed51077b4ff
https://pubmed.ncbi.nlm.nih.gov/15165132

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