A Cascade Cycloaddition Strategy Leading to the Total Synthesis of (−)-FR182877

Evans, David A.; Starr, Jeremy T.

doi:10.1002/1521-3773(20020517)41:10<1787::aid-anie1787>3.0.co;2-v

Cited by 124 publications

(45 citation statements)

References 33 publications

(23 reference statements)

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“…20 A research team led by Takamura, Arimoto, and Uemura used this method to assemble the polycyclic skeleton of nakiterpiosin. 21 Heating macrolide 38 at 160 °C gave 39 and 40 as a mixture of diastereomers in good yield.…”

Section: Synthesis Of C-nor-d-homosteroidsmentioning

confidence: 99%

The Chemistry and Biology of Nakiterpiosin – C-nor-D-Homosteroids

Gao

Wang

et al. 2012

Synlett

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Section: Synthesis Of C-nor-d-homosteroidsmentioning

confidence: 99%

The Chemistry and Biology of Nakiterpiosin – C-nor-D-Homosteroids

Gao

Wang

et al. 2012

Synlett

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“…It was not until the first total synthesis of the reported (albeit unnatural) enantiomer was completed by Sorensen that the structure was reassigned [160,161]. The natural enantiomer has been synthesized by Sorensen [162] and Evans [163]. The biology of cyclostreptin is very interesting.…”

Section: Cyclostreptinmentioning

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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“…Since a variety of 1-alkenylboron compounds, including (E)-and (Z)-isomers, are now available, the alkenyl-alkenyl coupling reaction has been used for the synthesis of various biologically active natural products, including: a macrolide antibiotic, rutamycin B [313]; (5Z,8Z,10E,12R,14Z)-12-hydroxy-5,8,10,14-icosatetraenoic acid [(12R)-HETE] [314], an antiproliferative agent; (þ)-curacin A [298], an aglycone of chlorothricin; (-)-chlorothricolide [315], a member of a small family of C 15 lupinine alkaloids; (þ)-aloperine [316], restrictinols that exhibit antifungal activity [317]; marine alkaloids, (-)-lepadins A, B, and C [318]; a highly unsaturated 20-membered macrocyclic system having four carbohydrate units, apoptolidin [14]; and cytotoxic substances FR 182877 and clinic acid [319]. The synthesis of polyene natural products via metal-catalyzed protocol has recently been reviewed [320].…”

Section: Reactions Of B-alkenyl Compoundsmentioning

confidence: 99%