Synthetic Studies on the Narciclasine Alkaloids. A Synthesis of (±)-Lycoricidine

Martin, Stephen F.; Tso, Hsi-Hwa

doi:10.3987/com-92-s31

Cited by 63 publications

(14 citation statements)

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“…the synthesis of (+)-lycoricidine was found in 1991 by Ogawa's group [101] and further exploited by others [95,104,105]. This synthesis used aminocyclitol 71 prepared by the route described in Schema 11 via the cyclohexenone 70.…”

Section: Iii-2-2) Intramolecular Coupling Of the A-ring And Preformedmentioning

confidence: 97%

“…Deprotection of 84 gave lycoricidine obtained in 9 steps from bromobenzene. Martin explored the same approach in a formal synthesis of racemic lycoricidine [104]. The aminocyclitol 88 was prepared by hetero-Diels-Alder reaction of the protected diol 86 with benzyl nitrosocarbamate to give adduct 87 in 69% yield [111].…”

Section: Iii-2-2) Intramolecular Coupling Of the A-ring And Preformedmentioning

confidence: 99%

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Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Chapleur¹,

Chrétien²,

Ahmed³

et al. 2006

COS

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Plants of the genus Amaryllidaceae produce a number of alkaloids and other non-basic related molecules, some of them showing antitumor activities. The low availability of these often-complex structures, coupled with their interesting biological properties, has stimulated a long-standing interest in the chemistry community. Total syntheses of challenging structures such as lycoricidine, narciclasine and pancratistatin, which are highly oxygenated tetracyclic systems comprising up to six contiguous chiral centers on ring C, have been accomplished. These well-known structures, more than thirty years for lycoricidine, continue to stimulate interest in synthetic work to provide enough synthetic material or analogs, and also are a model target to test or develop new synthetic methodologies. The synthetic studies around these complex phenanthridinones made use of the latest up-to-date synthetic methodologies and led to the development of novel methods of functionalization and carbon-carbon bond formation. The purpose of this review is to summarize recent total syntheses and synthetic approaches towards these three highly oxygenated members of this particular class of alkaloids over the last twenty years. The review is arranged according to the different strategies used for the construction of the benzophenanthridinone ring system.

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Section: Iii-2-2) Intramolecular Coupling Of the A-ring And Preformedmentioning

confidence: 97%

Section: Iii-2-2) Intramolecular Coupling Of the A-ring And Preformedmentioning

confidence: 99%

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Chapleur¹,

Chrétien²,

Ahmed³

et al. 2006

COS

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“…All of the previous approaches to the narciclasine skeleton that utilize aHeck coupling had required aprotected amine, [81,82,85,183] and therefore the secondary amide nitrogen of amide 416 was protected prior to the key Heck coupling step.Several conditions for the Heck reaction were screened and the desired product 417 was obtained only under the conditions shown (Scheme 85). With the coupled product 417 in hand, full deprotection afforded 7-aza-nornarciclasine (418).…”

Section: Gonzalez (2011) -A-ring Analogues Of (+ +)-Pancratistatinmentioning

confidence: 99%

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

et al. 2016

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This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. Discussion of biological activities is provided for unnatural derivatives. Future prospects and further developments in this area are covered at the end of the review. The literature is covered to the end of August 2015.

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“…427 [190,[514][515][516] (+)-Lycoricidine One of the most remarkable applications is the one reported for the construction of the skeleton of taxol (402) [574] by an 8-exo-trig cyclization of the enol triflate 400 [301a,b] (Scheme 8.79). The ring closure of the eight-membered ring to complete the rigid and compact tricyclic system is not trivial [145].…”

Section: Syntheses Of Heterocycles Natural Products and Other Biolomentioning

confidence: 99%

Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

Bräse¹,

Meijere²

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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The carbopalladation of an alkene by an organylpalladium halide is the essential step in one of the major contemporary metal-catalyzed C-C coupling reactions. About 45 years ago, a Japanese and an American group almost simultaneously designed and executed palladium-mediated coupling reactions of aryl and alkenyl halides with alkenes [1]. In subsequent investigations, Richard Heck and his group developed this reaction into a catalytic transformation and started to demonstrate its usefulness as well as its rather broad scope. The real push to utilize this powerful C-C-bondforming process, however, started only around the mid-1980s, and by now, an impressive number of publications have established the meanwhile so-called Heck reaction [2] 1) as an indispensable method in Organic Synthesis [3][4][5][6][7]. The universal recognition of the importance of the Heck reaction and the Negishi as well as the Suzuki coupling eventually won the Nobel Prize for Richard Heck along with Ei-ichi Negishi and Akira Suzuki in 2010. The applications of the Heck reaction range from the preparation of -functionalized and unfunctionalized -hydrocarbons, novel polymers, and dyes to new advanced enantioselective syntheses of natural products and biologically active nonnatural compounds. The more or less simultaneous developments of mechanistically related variants, namely, the Kumada, Suzuki, Stille, Hiyama, and Negishi coupling reactions (Chapters 12, 2, 3, 4, and 15, respectively) of metallated alkenes and arenes with aryl and alkenyl halides or the metal-catalyzed formation and cycloisomerization of enynes have drawn profit from the improvement of and mechanistic insights into the Heck reaction. This, of course, applies vice versa as well. Using only a catalytic amount of a palladium(0) complex or a precursor to a palladium species, the Heck reaction can bring about unprecedented structural changes, particularly when conducted intramolecularly. The full potential of this palladium-catalyzed process is still being further explored as demonstrated by a total of over 7000 publications in the past 40 years by 1) The alkynylation of aryl and alkenyl halides, frequently also considered as Heck reactions, is described in Chapter 6.

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Synthetic Studies on the Narciclasine Alkaloids. A Synthesis of (±)-Lycoricidine

Cited by 63 publications

References 0 publications

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

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