Diversity-oriented synthesis of bicyclic and tricyclic alkaloids.

A diversity-oriented synthesis involving a cascade sequence, taking linear aminoalkenes to polycyclic scaffolds reminiscent of natural alkaloids, is presented.

[1]  David R Spring,et al.  Diversity-oriented synthesis. , 2009, Chemical record.

[2]  Stefan Wetzel,et al.  Interactive exploration of chemical space with Scaffold Hunter. , 2009, Nature chemical biology.

[3]  David R Spring,et al.  Is synthesis the main hurdle for the generation of diversity in compound libraries for screening? , 2009, Expert opinion on drug discovery.

[4]  Andreas Bender,et al.  The discovery of antibacterial agents using diversity-oriented synthesis. , 2009, Chemical communications.

[5]  I. Coldham,et al.  Synthesis of fused tricyclic amines from enolizable acyclic aldehydes by cyclization then dipolar cycloaddition cascade: synthesis of myrioxazine A. , 2009, Organic letters.

[6]  K. Tomioka,et al.  Total synthesis of (-)-lycorine and (-)-2-epi-lycorine by asymmetric conjugate addition cascade. , 2009, Organic letters.

[7]  F. J. Fañanás,et al.  A palladium(II)-catalyzed synthesis of spiroacetals through a one-pot multicomponent cascade reaction. , 2009, Angewandte Chemie.

[8]  Ming Li,et al.  Application of ortho-chloro-β-aroylthioamides in synthesis(II): an efficient one-pot, three-component synthesis of tricyclic thiochromeno[2,3-b]pyridine derivatives , 2009 .

[9]  P. Hanson,et al.  "Click, click, cyclize": a DOS approach to sultams utilizing vinyl sulfonamide linchpins. , 2009, Organic letters.

[10]  Stephen F. Martin,et al.  Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. , 2009, Chemistry.

[11]  A. Mann,et al.  Hydroformylation of homoallylic azides: a rapid approach toward alkaloids. , 2009, Organic letters.

[12]  Stuart L. Schreiber,et al.  Organic chemistry: Molecular diversity by design , 2009, Nature.

[13]  Yu Du,et al.  Total synthesis of (-)-ardeemin. , 2009, The Journal of organic chemistry.

[14]  Adam Nelson,et al.  Synthesis of Natural-Product-Like Molecules with Over Eighty Distinct Scaffolds** , 2008, Angewandte Chemie.

[15]  David R Spring,et al.  Identification of an anti-MRSA dihydrofolate reductase inhibitor from a diversity-oriented synthesis. , 2008, Chemical communications.

[16]  F. Lévesque,et al.  A versatile cascade of intramolecular Vilsmeier-Haack and azomethine ylide 1,3-dipolar cycloaddition toward tricyclic cores of alkaloids. , 2008, Organic letters.

[17]  David R Spring,et al.  Gemmacin B: bringing diversity back into focus. , 2008, Organic & biomolecular chemistry.

[18]  David R Spring,et al.  Exploiting domino enyne metathesis mechanisms for skeletal diversity generation. , 2008, Chemical communications.

[19]  Adam Nelson,et al.  Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries , 2008, Natural product reports.

[20]  Andreas Bender,et al.  Anti-MRSA agent discovery using diversity-oriented synthesis. , 2008, Angewandte Chemie.

[21]  Andreas Bender,et al.  Diversity-oriented synthesis; a spectrum of approaches and results. , 2008, Organic & biomolecular chemistry.

[22]  Stuart L Schreiber,et al.  Towards the optimal screening collection: a synthesis strategy. , 2008, Angewandte Chemie.

[23]  A. Córdova,et al.  One-pot catalytic asymmetric cascade synthesis of cycloheptane derivatives. , 2008, Chemistry.

[24]  H. Adams,et al.  Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine. , 2007, Angewandte Chemie.

[25]  R. Hsung,et al.  An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine. , 2007, The Journal of organic chemistry.

[26]  D. Enders,et al.  Asymmetric organocatalytic domino reactions. , 2007, Angewandte Chemie.

[27]  K C Nicolaou,et al.  Cascade reactions in total synthesis. , 2006, Angewandte Chemie.

[28]  L. Fensterbank,et al.  Tandem Radical Reactions , 2006 .

[29]  Suzanne Fergus,et al.  Skeletal diversity construction via a branching synthetic strategy. , 2006, Chemical communications.

[30]  M. Rejžek,et al.  Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline fragmentation. , 2005, Chemical communications.

[31]  M. Rejžek,et al.  Combining two-directional synthesis and tandem reactions: an efficient strategy for the total syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine. , 2005, Organic & biomolecular chemistry.

[32]  W. Kitching,et al.  Spiroacetal biosynthesis: (+/-)-1,7-dioxaspiro[5.5]undecane in Bactrocera cacuminata and Bactrocera oleae (Olive Fruit Fly). , 2005, Organic letters.

[33]  M. Malacria,et al.  N-Silyl-Tethered Radical Cyclizations: A New Synthesis of γ-Amino Alcohols , 2003 .

[34]  M. Rejžek,et al.  Two-directional synthesis. Part 2: An expedient entry into the quinolizidine skeleton , 2002 .

[35]  A. Guarna,et al.  A Short and Efficient Route to Enantiopure 3,5-Diarylpyrrolizidines. , 1999, The Journal of organic chemistry.

[36]  J. Braekman,et al.  Complete assignment of the 1H and 13C NMR spectra of the Coccinellidae‐defensive alkaloids myrrhine, precoccinelline and hippodamine, their N ‐oxides and the corresponding hydrochlorides , 1999 .

[37]  L. Tietze Domino Reactions in Organic Synthesis. , 1996, Chemical reviews.

[38]  Y. Nagao,et al.  NEW REACTION MODE OF THE DIECKMANN-TYPE CYCLIZATION UNDER THE LEWIS ACID-ET3N CONDITIONS , 1995 .

[39]  R. M. Dipardo,et al.  Stereo- and regioselective total synthesis of the hydropyrido[2,1,6-de]quinolizine ladybug defensive alkaloids , 1984 .

[40]  R. Eisner,et al.  A total synthesis of myrrhine, (±)-hippodamine, and (±)-convergine , 1976 .

[41]  R. Newton,et al.  Stereochemical studies of nitrogen bridgehead compounds by spectral means , 1971 .

[42]  C. Rader,et al.  Azabicyclic Alcohols. III. Stereochemistry of the 7- and 8-Hydroxyindolizidines1 , 1965 .

[43]  T. Eisner,et al.  Hemorrhage in a Coccinellid Beetle and Its Repellent Effect on Ants , 1961, Science.

[44]  Jared T. Shaw,et al.  Naturally diverse: highlights in versatile synthetic methods enabling target- and diversity-oriented synthesis. , 2009, Natural product reports.

[45]  Dongmei Cui,et al.  Supplementary Material (ESI) for Chemical Communications , 2009 .

[46]  F. Boyer,et al.  Substituent effects in tandem ring-closing metathesis reactions of dienynes , 2006 .

[47]  B. Tursch,et al.  Chemical ecology of arthropods-X. The structure of myrrhine and the biosynthesis of coccinelline , 1975 .

[48]  M. Rejžek,et al.  Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry Combining Two-directional Synthesis and Tandem Reactions, Part 11: Second Generation Syntheses of (±)-hippodamine and (±)-epi-hippodamine , 2022 .