78592-77-5

Upstream product

• 78592-82-2 4-(tert-butyldimethylsilyloxy)-1-butyne 
• 75-24-1 trimethylaluminum 
• 78592-73-1 (E)-4-iodo-3-methylbut-3-en-1-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 88968-96-1 5-((tert-Butyldimethylsilyl)oxy)-3-methyl-2(E)-pentenoic Acid 
• 527755-03-9 (4R,5S,6S)-6-[(E)-1,5-dimethylhex-1-enyl]-4-hydroxy-5-methoxycyclohex-2-enone 
• 527755-05-1 (2S,3S,4R,5R)-4-hydroxy-3-methoxy-5-methyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527755-11-9 (2S,3S,4R,5R)-4-hydroxy-3-methoxy-5-ethyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-86-5 (4R)-4-benzyl-3-[(3E)-3,7-dimethylocta-3-enoyl]oxazolidin-2-one 
• 527755-07-3 (2S,3S,4R,5R)-4-trimethylsilyloxy-3-methoxy-5-methyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-96-7 (4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone 
• 527754-98-9 (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-94-5 (4S)-4-((1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl)-5,9-dimethyldeca-1,5-dien-3-one 
• 527755-39-1 (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one 
• 527755-34-6 (2S,3S,4R,5S)-2-((E)-1,5-dimethylhex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-5-methylcyclohexanone 
• 527754-99-0 (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 
• 527755-13-1 (2S,3S,4R,5R)-4-benzoyloxy-5-ethyl-3-methoxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527755-36-8 (3R,4S,5S,6R,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-7-methyl-1-oxaspiro[2.5]octane 

Relevant academic research and scientific papers

Efficient and stereo-selective syntheses of three stereoisomers of the sex pheromone of the cowpea weevil, Callosobruchus maculatus

An efficient and stereoselective synthesis of three stereoisomers of the sex pheromone of the cowpea weevil, Callosobruchus maculatus, is reported.

Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin

A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.

Diastereo- A nd Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers

A Cu-catalyzed method for the efficient enantio- A nd diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable ?,?-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.

Synthesis of the macrolactone structure of the aurisides

The core structure of the aurisides has been reached by the coupling of three subunits including as key step a cross-metathesis/hydrogenation/ketalisation sequence, the addition of a vinyl lithium derivative onto an aldehyde and finally a lactonization un

Synthesis of the C1-C13 fragment of (+)-callipeltoside A

The synthesis of the C1-C13 fragment of (+)-callipeltoside A has been achieved in 12 steps with an overall yield of 11%. Georg Thieme Verlag Stuttgart.

Diastereoselective Additions of Chiral Vinylzinc Reagents to α-Chiral Aldehydes

(Matrix presented) Additions of vinylic zinc bromide reagents to α-chiral aldehydes (R1 = CH2OTBS, R2 = Me; R1 = Me, R2 = OTBS) in the presence of lithiated (+)- or (-)-N-methylephedrine proceed with

MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

Synthetic studies towards the phomactins. Concise syntheses of the tricyclic furanochroman and the oxygenated bicyclo[9.3.1]pentadecane ring systems in phomactin A.

A concise synthesis of the tricyclic furanochroman unit 3 found in the PAF antagonist phomactin A (1) isolated from the marine fungus Phoma sp., is described. In complementary studies, a variety of synthetic routes towards the bicyclo[9.3.1]pentadecane ring system 4 in phomactin A were explored. These studies culminated in a synthesis of the substituted ring system 79 containing all the carbon atoms and all the necessary oxygen centres for elaboration to phomactin A itself.

Efficient assembly of the phomactin core via two different macrocyclization protocols.

[reaction--see text] The core structure of phomactins C and D was assembled by an efficient strategy starting from 3,4-dimethylcyclohexen-2-one. Key reactions include (1) a high yielding and highly diastereoselective Michael addition of a mixed cuprate, (

Transannular Diels-Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors

Transannular Diels-Alder reactions on 14-membered macrocycles containing properly located diene and methyl-substituted dienophile units lead to A.B.C. tricycles related to steroids.To study the influence of the olefin and diene geometry on the stereochemical outcome of the Diels-Alder reaction it was necessary to prepare macrocyclic trienes of well-defined stereochemistry.Eight different types of macrocyclic trienes might be obtained by the coupling of appropriate dienophiles and dienes, namely, TTC, TTT, TCC, TCT, CTC, CTT, CCC, and CCT.In this paper (first in a series of two), the synthesis of appropriately functionalized dienophile and diene synthons, as well as their coupling reaction affording macrocyclic triene precursors, is described.