442913-72-6

Upstream product

• 334972-54-2 (S)-tert-butyl((2-((4-methoxybenzyl)oxy)hex-5-en-1-yl)oxy)dimethylsilane 
• 334972-53-1 (S)-1-((tert-butyldimethylsilyl)oxy)hex-5-en-2-ol 
• 764-59-0 hex-5-en-1-al 
• 442913-70-4 3-(2-hydroxy-hex-5-enoyl)-4-isopropyl-oxazolidin-2-one 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 127102-61-8 (S)-hex-5-ene-1,2-diol 
• 934545-49-0 (S)-2-((4-methoxybenzyl)oxy)hex-5-en-1-ol 
• 934545-47-8 C₁₄H₁₈O₃ 
• 10353-53-4 1,2-epoxy-5-hexene 
• 442913-71-5 4-isopropyl-3-[2-(4-methoxy-benzyloxy)-hex-5-enoyl]-oxazolidin-2-one 

Downstream Products

• 934545-53-6 C₂₅H₃₆O₆ 
• 442913-68-0 (E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one 
• 934545-55-8 C₂₃H₃₂O₆ 
• 442913-67-9 (S)-2-(4-Methoxy-benzyloxy)-hex-5-enoic acid (S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-butyl ester 

Relevant academic research and scientific papers

First total synthesis of pinolide

The first total synthesis of pinolide, a nonsymmetrical ten-membered macrocyclic, is described starting from readily available (-)-tartaric and L-ascorbic acid. The key synthetic steps include Barbier allylation, Yamaguchi esterification and ring-closing metathesis (RCM) reactions. The synthetic strategy has been successful for the construction of the ten-membered core skeleton. A facile and convergent approach enabled the incorporation of all the four stereogenic centers present in the molecule. The first total synthesis of pinolide, a nonsymmetrical ten-membered macrocycle having four stereogenic centers has been demonstrated. The stereoselective approach involves key reaction steps including Barbier allylation, Yamaguchi esterification, and Grubbs' ring-closing metathesis reactions. Copyright

Formal synthesis of pinolide via l-proline-catalyzed sequential α-aminooxylation, Horner-Wadsworth-Emmons olefination and Sharpless asymmetric dihydroxylation

A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of l-proline catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule.

Total synthesis and evaluation of the actin-binding properties of microcarpalide and a focused library of analogues

A comparative investigation shows that hydroxylated 10-membered lactones modeled around the fungal metabolites microcarpalide (1) and pinolidoxin (2) are endowed with selective actin-binding properties. Although less potent than the marine natural product

Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle

A concise approach to a family of potent herbicidal 10-membered lactones is described on the basis of ring-closing metathesis (RCM) as the key step for the formation of the medium-sized ring. This includes the first total syntheses of herbarumin I (1) and