ChemInform Abstract: Applications of C-H Insertion Reaction in Total Synthesis of Biologically Active Heterocyclic Natural Products

ChemInform ◽  
2016 ◽  
Vol 47 (12) ◽  
pp. no-no
Author(s):  
Toshiyuki Kan ◽  
Tomohiro Asakawa ◽  
Makoto Inai
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Biologically Active ◽  
Insertion Reaction

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.

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

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

2011 ◽  
Vol 84 (6) ◽  
pp. 1379-1390 ◽  
Author(s):  
Michael C. McLeod ◽  
Margaret A. Brimble ◽  
Dominea C. K. Rathwell ◽  
Zoe E. Wilson ◽  
Tsz-Ying Yuen
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electronic Properties ◽  
Late Stage ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Berkelic Acid ◽  
Synthetic Approaches

Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.

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