Synthesis of the Tetracyclic ABCD Ring Domain of Calyciphylline A-Type Alkaloids via Reductive Radical Cyclizations

被引：29

作者：

Coussanes, Guilhem ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, IBUB, Lab Quim Organ, Av Joan XXIII S-N, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 04期

关键词：

DAPHNIPHYLLUM ALKALOIDS; TRICYCLIC CORE; EXPEDIENT CONSTRUCTION; (-)-CALYCIPHYLLINE N; MICHAEL ADDITION; SYSTEM; TRICHLOROACETAMIDES; DAPHNICYCLIDIN; ENAMIDES; SKELETON;

D O I：

10.1021/acs.orglett.7b00035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tetracyclic compound with the ABCD ring framework of calyciphylline A-type alkaloids was synthesized from a cis-3a-methyloctahydroindole triggered by a 5-endo radical cyclization. The synthesis required two additional ring-forming steps: the construction of a seven-membered ring by aldol cyclization and the azabicyclic fragment by a radical ring closure of a trichloroacetamide-tethered enol acetate followed by a diastereoselective alpha-methylation of the lactam group.

引用

收藏

页码：878 / 881

页数：4

相关论文

共 47 条

[1] The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis [J].

Bradshaw, Ben ;

Bonjoch, Josep .

SYNLETT, 2012, (03) :337-356

[2] β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations.: A concise construction of the mesembrine skeleton [J].

Cassayre, J ;

Quiclet-Sire, B ;

Saunier, JB ;

Zard, SZ .

TETRAHEDRON, 1998, 54 (07) :1029-1040

[3] Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes [J].

Cave, C ;

Desmaele, D ;

dAngelo, J ;

Riche, C ;

Chiaroni, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4361-4368

[4] Axially Chiral Enamides: Substituent Effects, Rotation Barriers, and Implications for their Cyclization Reactions [J].

Clark, Andrew J. ;

Curran, Dennis P. ;

Fox, David J. ;

Ghelfi, Franco ;

Guy, Collette S. ;

Hay, Benjamin ;

James, Natalie ;

Phillips, Jessica M. ;

Roncaglia, Fabrizio ;

Sellars, Philip B. ;

Wilson, Paul ;

Zhang, Hanmo .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13) :5547-5565

[5] Bond Rotation Dynamics of Enamides: The Effect of the Acyl Group and Potential for Chirality Transfer during 5-Endo Trig Radical Cyclizations [J].

Clark, Andrew J. ;

Curran, Dennis P. ;

Geden, Joanna V. ;

James, Natalie ;

Wilson, Paul .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4546-4551

[6] Stereodivergent reduction of enelactams embedded in hexahydroindoles.: Synthesis of traps-3-substituted-cis-3a-methyloctahydroindoles [J].

Cordero-Vargas, Alejandro ;

Bradshaw, Ben ;

Bonjoch, Josep .

TETRAHEDRON, 2008, 64 (35) :8134-8140

[7] A stereocontrolled entry to 3-functionalized cis-3a-methyloctahydroindoles:: Building blocks for Daphniphyllum alkaloid synthesis [J].

Cordero-Vargas, Alejandro ;

Urbaneja, Xavier ;

Bonjoch, Josep .

SYNLETT, 2007, (15) :2379-2382

[8]

Coussanes G, 2016, THESIS

[9] Radical Cyclization of Trichloroacetamides: Synthesis of Lactams [J].

Coussanes, Guilhem ;

Vila, Xavier ;

Diaba, Faiza ;

Bonjoch, Josep .

SYNTHESIS-STUTTGART, 2017, 49 (07) :1481-1499

[10] Expedient Construction of the [7-5-5] All-Carbon Tricyclic Core of the Daphniphyllum Alkaloids Daphnilongeranin B and Daphniyunnine D [J].

Darses, Benjamin ;

Michaelides, Iacovos N. ;

Sladojevich, Filippo ;

Ward, John W. ;

Rzepa, Paula R. ;

Dixon, Darren J. .

ORGANIC LETTERS, 2012, 14 (07) :1684-1687

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