A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene

Castoldi, Damiano; Caggiano, Lorenzo; Panigada, Laura; Sharon, Ofer; Costa, Anna M.; Gennari, Cesare

doi:10.1002/anie.200461767

Cited by 49 publications

(8 citation statements)

References 56 publications

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“…(221)) [1117,1118], hybrids of d-galactose with 1-deoxynojirimycin analogs [1119], the tetracyclic core of tetrapentalones [1120], 1-epi aglycon of cripowellins A and B [445], gambieric acid [1121], aspercyclide C [524], radicicol and pochonin C [1122], trachelanthamidine [1123], heliannuols G and H [652], (−)-Geismann-Waiss lactone [1124], tuberostemonines [688], (−)-kendomycin [1125], pochonin D [1126], (−)-223A [1127], coleophomones B-D [1128], brevetoxin B [130], garsubellin A [45], fostriecin [48], 11-acetoxy-4-deoxyasbestin D [1129], (+)-cyclophellitol [1130], ␤-C-glycosides [50], zoapatanol [247], deoxymannojirimycin and swainsonine [1131], valienamine [1132], A 3 adenosine recetor agonists [1133], vincantril [810], (−)-perhydrohistrionicotoxin [1134], annonaceous acetogenins [1135], deoxycombrestatin A-4 analogs [1136], (+)-lentiginosine and analogs [1137], N-malayamycin A [1138], (−)-salicylhalamides A and B [938], oxytocin analogs [1139], steroid-like compounds [440], (−)-isoprelaurefucin [338], halichondrin B [1140], (−)-microcarpalide and (+)-lethaloxin [1141,1142], anamarine …”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…Eleutherobin has also been synthesized by Danishefsky [146][147][148] and Gennari [149,150]. A number of groups have been working on analogs [151][152][153][154] and an SAR has been established [140], however attempts to make simplified analogs have resulted in loss of potency [155,156].…”

Section: Eleutherobin/sarcodictyinsmentioning

confidence: 99%

Microtubule-Stabilizing Natural Products as Promising Cancer Therapeutics

Gallagher¹

2007

CMC

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Paclitaxel and related taxanes exhibit their anticancer activity by promoting tubulin polymerization and stabilizing microtubules, which results in mitotic G2/M arrest and apoptosis. The clinical success of paclitaxel in treating a wide array of tumor types has led to numerous efforts to identify novel natural products with paclitaxel-like mechanisms of action, but which may overcome some of the liabilities of the taxanes. Although the list of natural products that share the paclitaxel-like mechanism is relatively small, it continues to expand and currently includes a number of structurally distinct classes. Despite the mechanistic similarities between these classes, differences exist which may translate into their differential efficacy in the clinic. The past several years have seen a considerable amount of pre-clinical and clinical progress in developing these novel microtubule-stabilizing natural products as cancer therapeutics. This review focuses primarily on recent advances published since 2002.

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“…A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction was reported [77] (Scheme 61).…”

Section: Metathesismentioning

confidence: 99%

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

Hong¹,

Nimje

2006

COC

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The development of new catalytic reactions for C-C bond formation has played a significant role in natural products synthesis. In this article we review catalytic C-C bond formation with respect to the carbon atoms' hybridization and the products formed. The reactions of unusual substrates and the development of new reaction conditions and catalyst systems are included. This survey highlights the use of catalysts in natural products synthesis during the years 2000-2005.

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A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene

Cited by 49 publications

References 56 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Microtubule-Stabilizing Natural Products as Promising Cancer Therapeutics

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

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