334976-36-2

Upstream product

• 108-05-4 vinyl acetate 
• 334976-31-7 6-(benzyloxy)-hex-1-yn-3-ol 
• 1257220-58-8 (2R,3S)-2-[3-(benzyloxy)propyl]-3-(chloromethyl)oxirane 
• 5470-84-8 4-benzyloxybutanal 
• 364631-45-8 6-benzyloxy-hex-1-yn-3-one 

Downstream Products

• 364631-50-5 (2E,4R,5S,6R)-(+)-methyl-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxy-non-2-enoate ester 
• 364631-48-1 (2E,4R)-(+)-7-benzyloxy-4-methoxy-3-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-hept-2-en-1-ol 
• 364631-49-2 (2R,3R,4R)-(+)-7-benzyloxy-4-methoxy-3-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-hept-2,3-epoxy-1-ol 
• 364631-61-8 (2E,4R)-(-)-isopropyl-7-benzyloxy-4-methoxy-3-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-hept-2-en-1-oate ester 
• 364631-60-7 (2E,4R)-(-)-isopropyl-7-benzyloxy-4-hydroxy-3-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-hept-2-en-1-oate ester 
• 364631-63-0 (4R,5S,6R)-(+)-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxynonane-1-ol 
• 364631-62-9 (4R,5S,6R)-(+)-methyl-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxynonanoate ester 
• 364631-46-9 7-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-hept-2-ynoic acid isopropyl ester 
• 364631-53-8 (5S,6S)-5-Azido-6-((R)-4-benzyloxy-1-methoxy-butyl)-6-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-tetrahydro-pyran-2-ol 
• 364631-57-2 (3R,5S)-(+)-5-[(1'R)-4'-benzyloxy-1'-methoxybutyl]-5-[(4Z,1S,7S)-methyl-1-azido-7-methyloct-4-en-8-oate]-3-methyl-(3H)-furan-2-one 
• 364631-56-1 (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-ol 
• 364631-64-1 (4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol 
• 364631-51-6 2,2-Dimethyl-propionic acid 3-{(2R,3S)-3-((R)-4-benzyloxy-1-methoxy-butyl)-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-oxiranyl}-propyl ester 
• 364631-52-7 (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester 

Relevant academic research and scientific papers

Total synthesis of the phytotoxic stagonolides A and B

The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from d-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM.

A practical total synthesis of (+)-spirolaxine methyl ether

An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.

Total synthesis of (-)-stemospironine.

[structure: see text]. A stereocontrolled total synthesis of the polycyclic Stemona alkaloid, (-)-stemospironine (1) has been achieved. Key transformations include the use of a Staudinger reaction leading to the aza-Wittig ring closure of the perhydroazepine system. Formation of the vicinal pyrrolidine butyrolactone is described via the stereoselective intramolecular capture of an intermediate aziridinium salt.

A concise enantioselective synthesis of antimalarial febrifugine alkaloids.

Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.