Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II

2012 ◽  
Vol 10 (34) ◽  
pp. 6987-6994 ◽  
Author(s):  
Pradeep Kumar ◽  
Abhishek Dubey ◽  
Anand Harbindu
Keyword(s):  
Natural Products ◽  
Chiral Epoxides ◽  
Practical Synthesis

A very concise and practical synthesis of cascarillic acid, grenadamide and l-CCG-II, a cyclopropane containing natural products is accomplished employing Wadsworth-Emmons cyclopropanation reaction as key step.

scholarly journals A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

2013 ◽  
Vol 9 ◽  
pp. 1807-1812 ◽  
Author(s):  
Mark B Richardson ◽  
Spencer J Williams
Keyword(s):  
Fatty Acids ◽  
Natural Products ◽  
Selective Reduction ◽  
Isopropyl Group ◽  
Tertiary Alcohols ◽  
Practical Synthesis ◽  
Long Chain

A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C12–C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12–C14) or the C15and C16lactones pentadecanolide (for iso-C15–C17) and hexadecanolide (for iso-C18–C19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17and C18iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13–C16and C19iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.

ChemInform Abstract: Practical Synthesis of DOPA Derivative for Biosynthetic Production of Potent Antitumor Natural Products, Saframycins and Ecteinascidin 743.

ChemInform ◽  
2012 ◽  
Vol 43 (19) ◽  
pp. no-no
Author(s):  
Kohei Torikai ◽  
Takayoshi Saruwatari ◽  
Tatsuya Kitano ◽  
Takuya Sano ◽  
Atsuko Nakane ◽  
...  
Keyword(s):  
Natural Products ◽  
Practical Synthesis ◽  
Ecteinascidin 743

scholarly journals Practical Synthesis of DOPA Derivative for Biosynthetic Production of Potent Antitumor Natural Products, Saframycins and Ecteinascidin 743

2011 ◽  
Vol 8 (10) ◽  
pp. 686-689 ◽  
Author(s):  
Kohei Torikai ◽  
Takayoshi Saruwatari ◽  
Tatsuya Kitano ◽  
Takuya Sano ◽  
Atsuko Nakane ◽  
...  
Keyword(s):  
Natural Products ◽  
Practical Synthesis ◽  
Ecteinascidin 743

scholarly journals Acid-mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

2009 ◽  
Vol 5 ◽  
Author(s):  
Katsunori Tanaka ◽  
Koichi Fukase
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Natural Product ◽  
Residence Time ◽  
Temperature Control ◽  
Reactive Intermediate ◽  
Fast Reactions ◽  
New Strategy ◽  
Practical Synthesis

Microfluidic conditions were applied to acid-mediated reactions, namely, glycosylation, reductive opening of the benzylidene acetal groups, and dehydration, which are the keys to the practical synthesis of N-glycans and the immunostimulating natural product, pristane. A distinctly different reactivity from that in conventional batch stirring was found; the vigorous micromixing of the reactants with the concentrated acids is critical especially for the “fast” reactions to be successful. Such a common feature might be due to the integration of all favorable aspects of microfluidic conditions, i.e., efficient mixing, precise temperature control, and the easy handling of the reactive intermediate by controlling the residence time. The microfluidic reactions cited in this review indicate the need to reinvestigate the traditional or imaginary reactions which have so far been performed and evaluated only in batch apparatus, and therefore they could be recognized as a new strategy in synthesizing natural products of prominent biological activity in a “practical” and a “industrial” manner.

Practical Synthesis of Tricyclic Lactam Model of Antitumor Renieramycin-Saframycin Natural Products

Heterocycles ◽  
2016 ◽  
Vol 93 (2) ◽  
pp. 802
Author(s):  
Naoki Saito ◽  
Masashi Yokoya ◽  
Akiya Fujino ◽  
Ayako Yaguchi ◽  
Miku Yamazaki
Keyword(s):  
Natural Products ◽  
Practical Synthesis
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