An approach to total synthesis of (+)-lycoricidine

McIntosh, Matthias C.; Weinreb, Steven M.

doi:10.1021/jo00070a016

Cited by 97 publications

(47 citation statements)

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“…Mp: 102e103 C (Lit. 19 (s,3H),4.20 (q,J ¼ 7.4 Hz,1H), 5.23 (d,J ¼ 7.4 Hz,1H),7.02 (m,2H),7.11 (d,J ¼ 8.1 Hz,2H),7.15 (m,3H),7.56 (d,J ¼ 8.2 Hz,2H). 13 C NMR (CDCl 3 , 75 MHz): d (ppm) 10.6, 21.5, 30.7, 59.9, 126.7 (2C), 127.1 (2C), 127.…”

Section: N-(1-phenylpropyl)-tosylamide (15)mentioning

confidence: 99%

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

Zotto¹,

Michaux²,

Zarate-Ruiz³

et al. 2011

Journal of Organometallic Chemistry

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Section: N-(1-phenylpropyl)-tosylamide (15)mentioning

confidence: 99%

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

Zotto¹,

Michaux²,

Zarate-Ruiz³

et al. 2011

Journal of Organometallic Chemistry

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“…with reaction times from 30 min to 22 h, [54][55][56][57][58][59][60][61][62][63] whereas in other cases the same reaction was reported to take place in less than one hour at -78°C. [64,65] This suggested two alternative pathways: one fast, taking place even at -78°C, and another one slow, going through the phosphorane 52 (Scheme 7). Two papers seemed particularly interesting to us: Bestmann reported that better yields could be obtained by addition of CBr 4 to the mixture of aldehyde and PPh 3 , [66] whereas Weinreb, in his total synthesis of licoricidin, [64] faced a situation similar to ours -under the classical conditions (high temperature) only aldehyde decomposition was observed, whereas, upon mixing all three reagents at -78°C, a very fast reaction (only 5 min) gave the expected product in good yields.…”

Section: Resultsmentioning

confidence: 99%

Enzymatically Asymmetrised Chiral Building Blocks for the Synthesis of Complex Natural Product Analogues: The Synthesis of Dynemicin Analogues from 2‐(Quinolin‐4‐yl)propane‐1,3‐diol

et al. 2010

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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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An approach to total synthesis of (+)-lycoricidine

Cited by 97 publications

References 0 publications

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

Enzymatically Asymmetrised Chiral Building Blocks for the Synthesis of Complex Natural Product Analogues: The Synthesis of Dynemicin Analogues from 2‐(Quinolin‐4‐yl)propane‐1,3‐diol

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

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