1194667-20-3

Upstream product

• 99838-68-3 (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 87604-53-3 (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane 
• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 100-39-0 benzyl bromide 
• 942137-19-1 (2R)-2-[(1S)-1-(benzyloxy)-3-butenyl]-1,4-dioxaspiro[4.5]decane 
• 164145-69-1 1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 

Downstream Products

• 1239889-37-2 C₁₉H₃₀O₃Si 
• 66018-41-5 zeaenol 

Relevant academic research and scientific papers

Attempts towards the synthesis of mupirocin-H

The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated allyl Grignard reaction with Rglyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H. {figure presented}

Selective synthetic method of natural products Xylapyrroside A

The invention belongs to the field of chemical synthesis, and relates to a selective synthetic method of natural products Xylapyrroside A. According to the invention, (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-formaldehyde is taken as an initial raw material, a Grignard reaction, hydroxy benzyl protection, acetonide protection removal, hydroxy selective tert-butyl dimethyl silicon and benzyl protection, terminal double bond epoxidation and iodo ring opening and oxidation are carried out to obtain (4S,5R)-4,5-di-benzyloxy-6-tert-butyldimethylsilyloxy-1-n-amyl iodide-2-ketone, the product is subjected to condensation with another intermediate 5-(((tetrahydro-2H-pyrans-2-group)oxygen)methyl)-1H-pyrroles-2-formaldehyde under alkaline condition, and then the product is subjected to deprotection and cyclization, and finally the target product is synthesized. The method has the advantages of simple operation and high yield, and a reagent has the advantages of low cost and easy acquisition of the raw materials.

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: Isolation, complete structure elucidation, and total syntheses

Two new [named xylapyrrosides A (1) and B (2)] along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the EtOH extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A1 (1a), A2 (1b) and B1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs).

The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactoniza

Synthesis of the unusual α-amino acid component of some novel histone deacetylase inhibiting cyclic peptides

A flexible protocol for the synthesis of three lipophilic α-amino acid components of some novel cyclic peptides having important histone deacetylase inhibiting properties has been developed from a common source, which featured a cross-metathesis reaction

Stereoselective total synthesis of cytotoxic sporiolide A

A simple and highly efficient stereoselective total synthesis of cytotoxic agent sporiolide A has been achieved starting from d-mannitol; the strategy of synthesis utilizes stereoselective zinc-mediated allylation, aldol coupling and ring-closing metathes

Concise synthesis of five-membered ring carbasugars based on key ring-closing metathesis

A simple and efficient approach to the synthesis of five-membered ring carbasugars is achieved starting from readily available (R)-2,3-O- isopropylideneglyceraldehyde (2) through key ring-closing metathesis (RCM) in high overall yield. We have also confir

Asymmetric synthesis of Goniothalesdiol A from (R)-2,3-O-cyclohexylidine glyceraldehyde

Goniothalesdiol A 1 has been synthesized from (R)-2,3-O-cyclohexylidine glyceraldehyde with high stereoselectivity and 22% overall yield in 11 simple steps. The key features of the synthetic strategy include the stereocontrolled allylation of (R)-2,3-O-cy