Total synthesis

About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.

Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (±)-Rocaglamide

Abstract: The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide.

Enantioselective synthesis of paraconic acids.

Abstract: The development of a new method for the enantioselective synthesis of disubstituted γ-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (−)-roccellaric acid, (−)-nephrosteranic acid and (−)-protopraesorediosic acid, and the formal total synthesis of (−)-methylenolactocin and (−)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I)-catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.

Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2

Abstract: Cyclization Methods Related to the Synthesis of Macrolide Antibiotics.- Progress in the Total Synthesis of Spirotetronic Acid Macrolide Antibiotics.- Convergent Stereospecific Total Synthesis of Monocillin I and Monorden (or Radicicol).- Recent Progress in the Chemical Modification of Erythromycin.- Chemistry of FK - 506.- The "Enediyne" Antibiotics Calicheamicin ?1I, Esperamicin-Ar and Dynemicin-A: Physicochemical and Biological Properties-Partial and Total Synthesis.- Synthesis and Chemistry of Neocarzinostatin Analogs.- Synthesis of Nogalamycin and Related Substances.- Total Synthesis of Aryl C-Glycoside Antibiotics.- Total Synthesis of the Antifungal Antibiotic Ambruticin.- Synthetic Approaches to Methylenomycin B and Analogs.- The Orthosomycin Antibiotics.- ? -Unsubstituted ? -Lactams as Synthons for Antibiotics.- Chemistry and Synthesis of some Novel ? -Lactam Antibiotics and ? -Lactamase Inhibitors.- Recent Advances in the Chemistry and Biochemistry of ? -Lactams as ? -Lactamase Inhibitors.- Chemistry of Biologically Important Hydroxylated Indolizidines Synthesis of Swainsonine, Castanospermine and Slaframine.- The Chemistry and Total Synthesis of Mevinolin and Related Compounds.- Synthetic Efforts Towards Cerulenin and Tetrahydrocerulenin.

Total synthesis of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine.

Abstract: The first total syntheses of new monoterpene alkaloids (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct an appropriately trisubstituted cyclopentanone, followed by ring closure to the cis-perhydro-2-pyrindine skeleton by means of a reductive Heck-type reaction. Furthermore, topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives in the solid state for the stereospecific construction of a 1,2,3,4-tetrasubstituted cyclobutane ring was also investigated as a means to access (-)-incarvillateine.