Approaches to the stereoselective total synthesis of biologically active natural products

2005 ◽  
Vol 77 (1) ◽  
pp. 103-117 ◽  
Author(s):  
Anne Baron ◽  
Matthew Ball ◽  
Benjamin Bradshaw ◽  
Sam Donnelly ◽  
Olivier Germay ◽  
...  
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Total Synthesis ◽  
Recent Work ◽  
Biologically Active ◽  
Total Syntheses ◽  
Trisubstituted Double Bond ◽  
Epothilone B ◽  
Active Natural

Total syntheses of epothilone B and pamamycin 607, which feature reactions between functionalized allylstannanes and aldehydes to introduce a (Z)-trisubstituted double-bond and remote stereocenters stereoselectively, are discussed. Recent work concerned with carrying out this chemistry without the use of allylstannanes as starting materials and progress toward a total synthesis of bryostatins are also presented.

Recent results toward the stereoselective synthesis of biologically active natural products

2007 ◽  
Vol 79 (2) ◽  
pp. 163-172 ◽  
Author(s):  
Luiz C. Dias ◽  
Luciana G. de Oliveira ◽  
Paulo R. R. Meira
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Cell Cultures ◽  
Stereoselective Synthesis ◽  
Animal Cell ◽  
Biologically Active ◽  
Asymmetric Total Synthesis ◽  
Callystatin A ◽  
Animal Cell Cultures ◽  
Active Natural

This paper describes the convergent and stereocontrolled asymmetric total synthesis of (+)-crocacins C and D, potent inhibitors of animal cell cultures and several yeasts and fungi, and (-)-callystatin A, a potent antitumor polyketide.

scholarly journals Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

2009 ◽  
Vol 81 (2) ◽  
pp. 195-204 ◽  
Author(s):  
Stephen F. Martin
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Multicomponent Reactions ◽  
Nitrogen Heterocycles ◽  
Biologically Active ◽  
Total Syntheses ◽  
Biological Interest ◽  
Cascade Processes ◽  
Novel Applications ◽  
Active Natural

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1552-1571 ◽  
Author(s):  
Jianxian Gong ◽  
Zhen Yang ◽  
Yueqing Gu ◽  
Ceheng Tan
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Left Wing ◽  
Asymmetric Total Synthesis ◽  
Diversity Oriented Synthesis ◽  
Active Natural

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.1 Introduction2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids2.2 Synthesis of Left-Wing Fragment of Azadirachtin I2.3 Collective Synthesis of Cladiellins3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins3.2 Total Synthesis of Orientalol F3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C4 Summary and Outlook

Enantioselective constructions of quaternary carbons and their application to the asymmetric total syntheses of fredericamycin A and discorhabdin A

2007 ◽  
Vol 79 (4) ◽  
pp. 701-713 ◽  
Author(s):  
Yasuyuki Kita ◽  
Hiromichi Fujioka
Keyword(s):  
Natural Products ◽  
Optically Active ◽  
Biologically Active ◽  
Hypervalent Iodine ◽  
Total Syntheses ◽  
Carbon Centers ◽  
Phenol Derivatives ◽  
Fredericamycin A ◽  
Active Natural ◽  
Quaternary Carbons

An efficient enantioselective construction of quaternary carbons including spiro carbons is an area of intense interest due to the importance of these units as components of biologically active natural products. Prominent methods are presented for the synthesis of chiral, nonracemic quaternary carbon centers by (i) stereospecific rearrangement of optically active epoxides, (ii) enzyme-catalyzed resolution, and (iii) hypervalent iodine reagent-induced ipso-substitution of para-substituted phenol derivatives. These methods were applied to the total syntheses of fredericamycin A and discorhabdin A.

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