Indolizidines and quinolizidines: natural products and beyond

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Editor: Prof. Joseph Philip Michael
University of the Witwatersrand
 
Alkaloids are assembled from a relatively small number of structural motifs. Among the motifs that are most frequently encountered are bicyclic systems containing bridgehead nitrogen - the indolizidines and quinolizidines. These two azabicyclic systems may occur in the natural products either in isolation or, more commonly, embedded within fused polycyclic arrays. It was estimated that between 25% and 30% of all alkaloids possess structures incorporating one or other of these motifs. Structural, spectroscopic and computational studies on both natural and synthetic indolizidines and quinolizidines are reported regularly. In this Thematic Series, there are representative articles covering several of these aspects. A number of authors have contributed reviews in which their own contributions to the development of indolizidine and quinolizidine chemistry are highlighted. There are articles on the total synthesis of relevant natural products, as well as articles describing novel methodological approaches to the systems of interest.

See also the Thematic Series:
Natural products in synthesis and biosynthesis II
Transition-metal and organocatalysis in natural product synthesis

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Indolizidines and quinolizidines: natural products and beyond

  • Joseph P. Michael

Beilstein J. Org. Chem. 2007, 3, No. 27, doi:10.1186/1860-5397-3-27

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Editorial
Published 26 Sep 2007

Flexible synthetic routes to poison- frog alkaloids of the 5,8-disubstituted indolizidine- class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A, (-)-205A, and (-)-219F

  • Naoki Toyooka,
  • Dejun Zhou,
  • Hideo Nemoto,
  • H. Martin Garraffo,
  • Thomas F. Spande and
  • John W. Daly

Beilstein J. Org. Chem. 2007, 3, No. 29, doi:10.1186/1860-5397-3-29

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Published 28 Sep 2007

Flexible synthesis of poison- frog alkaloids of the 5,8-disubstituted indolizidine- class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors

  • Soushi Kobayashi,
  • Naoki Toyooka,
  • Dejun Zhou,
  • Hiroshi Tsuneki,
  • Tsutomu Wada,
  • Toshiyasu Sasaoka,
  • Hideki Sakai,
  • Hideo Nemoto,
  • H. Martin Garraffo,
  • Thomas F. Spande and
  • John W. Daly

Beilstein J. Org. Chem. 2007, 3, No. 30, doi:10.1186/1860-5397-3-30

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Published 28 Sep 2007

A convenient allylsilane- N-acyliminium route toward indolizidine and quinolizidine alkaloids

  • Roland Remuson

Beilstein J. Org. Chem. 2007, 3, No. 32, doi:10.1186/1860-5397-3-32

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Review
Published 02 Oct 2007

An asymmetric synthesis of all stereoisomers of piclavines A1-4 using an iterative asymmetric dihydroxylation

  • Yukako Saito,
  • Naoki Okamoto and
  • Hiroki Takahata

Beilstein J. Org. Chem. 2007, 3, No. 37, doi:10.1186/1860-5397-3-37

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Published 29 Oct 2007

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

  • Roger Hunter,
  • Sophie C. M. Rees-Jones and
  • Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

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Published 03 Nov 2007

The enantiospecific synthesis of (+)-monomorine I using a 5-endo- trig cyclisation strategy

  • Malcolm B. Berry,
  • Donald Craig,
  • Philip S. Jones and
  • Gareth J. Rowlands

Beilstein J. Org. Chem. 2007, 3, No. 39, doi:10.1186/1860-5397-3-39

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Published 08 Nov 2007

A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine

  • Jian-Feng Zheng,
  • Wen Chen,
  • Su-Yu Huang,
  • Jian-Liang Ye and
  • Pei-Qiang Huang

Beilstein J. Org. Chem. 2007, 3, No. 41, doi:10.1186/1860-5397-3-41

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Published 08 Nov 2007

Synthesis of the Benzo- fused Indolizidine Alkaloid Mimics

  • Daniel L. Comins and
  • Kazuhiro Higuchi

Beilstein J. Org. Chem. 2007, 3, No. 42, doi:10.1186/1860-5397-3-42

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Published 30 Nov 2007

Synthesis of densely functionalized enantiopure indolizidines by ring- closing metathesis (RCM) of hydroxylamines from carbohydrate- derived nitrones

  • Marco Bonanni,
  • Marco Marradi,
  • Francesca Cardona,
  • Stefano Cicchi and
  • Andrea Goti

Beilstein J. Org. Chem. 2007, 3, No. 44, doi:10.1186/1860-5397-3-44

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Published 12 Dec 2007

Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds

  • Wolfgang Maison,
  • Marina Büchert and
  • Nina Deppermann

Beilstein J. Org. Chem. 2007, 3, No. 48, doi:10.1186/1860-5397-3-48

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Published 18 Dec 2007

Synthesis of crispine A analogues via an intramolecular Schmidt reaction

  • Ajoy Kapat,
  • Ponminor Senthil Kumar and
  • Sundarababu Baskaran

Beilstein J. Org. Chem. 2007, 3, No. 49, doi:10.1186/1860-5397-3-49

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Published 19 Dec 2007

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions

  • Giuditta Guazzelli,
  • Raffaello Lazzaroni and
  • Roberta Settambolo

Beilstein J. Org. Chem. 2008, 4, No. 2, doi:10.1186/1860-5397-4-2

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Published 15 Jan 2008

Knorr- Rabe partial reduction of pyrroles: Application to the synthesis of indolizidine alkaloids

  • Brendon S. Gourlay,
  • John H. Ryan and
  • Jason A. Smith

Beilstein J. Org. Chem. 2008, 4, No. 3, doi:10.1186/1860-5397-4-3

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Published 15 Jan 2008

Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

  • Annabella F. Newton,
  • Martin Rejzek,
  • Marie-Lyne Alcaraz and
  • Robert A. Stockman

Beilstein J. Org. Chem. 2008, 4, No. 4, doi:10.1186/1860-5397-4-4

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Published 17 Jan 2008

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl- 5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro- 2H-quinolizin- 1-yl]methanol

  • Joseph P. Michael,
  • Claudia Accone,
  • Charles B. de Koning and
  • Christiaan W. van der Westhuyzen

Beilstein J. Org. Chem. 2008, 4, No. 5, doi:10.1186/1860-5397-4-5

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Published 18 Jan 2008

Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E- 259B from a Bufonid toad (Melanophryniscus)

  • Angela Nelson,
  • H. Martin Garraffo,
  • Thomas F. Spande,
  • John W. Daly and
  • Paul J. Stevenson

Beilstein J. Org. Chem. 2008, 4, No. 6, doi:10.1186/1860-5397-4-6

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Published 21 Jan 2008

Total synthesis of the indolizidine alkaloid tashiromine

  • Stephen P. Marsden and
  • Alison D. McElhinney

Beilstein J. Org. Chem. 2008, 4, No. 8, doi:10.1186/1860-5397-4-8

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Published 26 Jan 2008
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