- Grob-Type Fragmentation Releases Paracyclophane Ring Strain in a Late-Stage Precursor of Haouamine A
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A ketene [2 + 2]-addition, an intramolecular aldol reaction, a Suzuki-Miyaura coupling, and a chemoselective lactam reduction were used to prepare a late-stage precursor of haouamine A. Exposure to acid led to a Grob-type fragmentation of the strained 3-aza[7]paracyclophane ring, followed by a tandem Pictet-Spengler reaction of the intermediate iminium ion and conversion to a novel 1,4a-propanocyclopenta[b]pyridine. This cascade reaction might also be relevant for the mechanism of action of the natural product.
- Cao, Liming,Wang, Chenbo,Wipf, Peter
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supporting information
p. 1538 - 1541
(2019/03/08)
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- Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)-H Bond Functionalization
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Herein we report a diastereoselective synthesis of medium-sized carbocycle-fused piperidines via [1,n (n = 6, 7)]-[1,5]-sequential hydride shift triggered double C(sp3)-H bond functionalization. When cinnamylidene malonates having N,N-dibenzyl propylamine moiety were treated with 5 mol % of Yb(OTf)3, a [1,6]-[1,5]-sequential hydride shift/cyclization process proceeded to afford seven-membered carbocycle-fused piperidines with excellent diastereoselectivities. This sequential system was applicable to the synthesis of eight-membered carbocycle-fused piperidines by an unprecedented [1,7]-[1,5]-sequential hydride shift/cyclization process.
- Kataoka, Miyabi,Otawa, Yuna,Ido, Natsuki,Mori, Keiji
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supporting information
p. 9334 - 9338
(2019/11/19)
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- Construction of seven-and eight-membered carbocycles by Lewis acid catalyzed C(sp3)-H bond functionalization
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We achieved a concise construction of seven-and eight-membered carbocycles via Lewis acid catalyzed C(sp3)-H bond functionalization. In these reactions, a quite rare [1,6 (or 7)]-hydride shift/cyclization process proceeded smoothly to afford seven-and eight-membered carbocycles with good chemical yields starting from substrates with high conformational freedom.
- Otawa, Yuna,Mori, Keiji
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supporting information
p. 13856 - 13859
(2019/11/21)
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- Highly efficient gold-catalyzed synthesis of dibenzocycloheptatrienes
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Dibenzocycloheptatrienes are obtained by a gold-catalyzed 7-exo-dig hydroarylation protocol in a highly efficient manner. The gold-catalyzed reaction usually gives the products in high yields and excellent selectivity. This procedure provides an easy and
- Pflaesterer, Daniel,Rettenmeier, Eva,Schneider, Severin,De Las Heras Ruiz, Edgar,Rudolph, Matthias,Hashmi, A. Stephen K.
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supporting information
p. 6752 - 6755
(2014/06/09)
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- Synthesis and structure activity relationships of cis- and trans- 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridines for 5-HT receptor subtypes
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A series of cis- and trans-fused hexahydroindeno[2,1-c]pyridines have been prepared and evaluated for affinity and selectivity at the 5-HT(1A) subtype of the serotonin receptor. Using molecular modeling studies we predicted that the 5-methoxy-trans-fused
- Meyer,DeBernardis,Hancock
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p. 105 - 112
(2007/10/02)
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