Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C

Hong, Bo; Li, Houhua; Wu, Ji‐Wei; Zhang, Jing; Lei, Xiaoguang

doi:10.1002/anie.201409503

Cited by 64 publications

(43 citation statements)

References 70 publications

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“…Then, the resulting enolate was approached by an aldehyde from the opposite side to the newly attached vinyl group. A similar stereochemical outcome of such transformation has been already reported [26–33]. Moreover, the addition of aldehyde gave rise to the anti aldol product (both in 25 and 26 ).…”

Section: Resultssupporting

confidence: 82%

“…A copper-catalyzed 1,4-addition of organometallic reagents to cyclic α,β-unsaturated ketones, followed by an aldol reaction has been already used in the synthesis of complex natural products [26–33]. Although this approach is challenging in terms of diastereoselectivity (up to eight possible diastereoisomers), it enables a rapid increase of molecular complexity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

Malik

Jarosz

2016

Beilstein J. Org. Chem.

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Synthesis of novel polyhydroxylated derivatives of decalin is described. The presented methodology consists in a one-pot copper-catalyzed 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivative of but-3-enal. The obtained diene is then subjected to an assisted tandem catalytic sequence: ring-closing metathesis with the subsequent reuse of the Ru-catalyst in the syn-dihydroxylation. The stereochemical outcome of these reactions is discussed.

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Section: Resultssupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

Malik

Jarosz

2016

Beilstein J. Org. Chem.

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“…[49] Thew ay that biosynthetic strategies employ divergent intramolecular cyclizationso facommon intermediate to produce diverse arrays of scaffolds inspired Mizoguchi et al to employ dehydrosecodine (73;S cheme 6) as ac ommon Scheme6. Biosynthesis-inspired approach to furnish diverse alkaloidal scaffolds.…”

Section: Emerging Strategies Towards the Concise And Efficient Constrmentioning

confidence: 99%

Scaffold Diversity Synthesis and Its Application in Probe and Drug Discovery

et al. 2016

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Scaffold diversity is a crucial feature of compound collections that has a huge impact on their success in biological screenings. The synthesis of highly complex and diverse scaffolds, which could be based on natural products, for example, is an arduous task that requires expertise in various aspects of organic synthesis and structural analysis. This challenge has been addressed by a number of synthesis designs, which employ natural products as a source of scaffold diversity, transform suitably designed common intermediates into various molecular frameworks, or entail highly concise synthetic routes to a number of distinct and complex scaffolds. In this Minireview, we highlight recent synthetic developments towards the construction of diverse and complex scaffolds and the application of the resulting compound collections in drug and probe discovery.

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“…N-methylindole was purchased from Aldrich and stored over 4 Å molecular sieves. N-ethylindole, [24] N-isopropylindole, [25] nBuNa, [26] and Mg(CH 2 SiMe 3 ) 2 [14] were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Atom Efficient Magnesiation of N‐Substituted Alkyl Indoles with a Mixed Sodium‐Magnesium Base

Stevens

Blair

2018

Eur J Inorg Chem

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This study presents the alkali metal mediated magnesiation (AMMMg) of three N-alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP) 2 Mg(CH 2 SiMe 3 )] 1 (TMEDA = N,N,N′,N′-tetramethylethylenediamine, TMP = 2,2,6,6-tetramethylpiperidine). All three magnesiated indoles have been successfully characterised by single-crystal X-ray diffraction and solution state NMR studies, whereas iodolysis and Pd-catalysed

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Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C

Cited by 64 publications

References 70 publications

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

Scaffold Diversity Synthesis and Its Application in Probe and Drug Discovery

Atom Efficient Magnesiation of N‐Substituted Alkyl Indoles with a Mixed Sodium‐Magnesium Base

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