83458-93-9

Upstream product

• 187745-66-0 methyl (3S)-6-(benzyloxy)-3-hydroxyhexanoate 
• 127793-67-3 (S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol 
• 83458-91-7 (2E)-6-(benzyloxy)hex-2-en-1-ol 
• 4541-14-4 4-benzyloxy-butan-1-ol 
• 5470-84-8 4-benzyloxybutanal 
• 1462-37-9 bromoethyl-2-benzyl ether 
• 299171-56-5 Methyl 6-(benzyloxy)-3-oxohexanoate 
• 13038-15-8 (E)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 133407-67-7 ethyl (E)-6-(benzyloxy)hex-2-enoate 
• 81518-74-3 1-benzyloxy-4-pentene 

Downstream Products

• 150055-68-8 (3S)-1,3-Bis(tert-butyldimethylsilyloxy)-6-benzyloxyhexane 
• 345319-57-5 (S)-4-(3-Benzyloxy-propyl)-2-(4-methoxy-phenyl)-[1,3]dioxane 
• 921207-68-3 ethyl (E)-(5S)-8-(benzyloxy)-5-hydroxy-2-octenoate 
• 921207-65-0 ethyl 2-{(2S,4S,6S)-6-[3-(benzyloxy)propyl]-2-phenyl-1,3-dioxan-4-yl}acetate 
• 299171-41-8 (S)-3-[(R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-methyl-3-phenylselanyl-dihydro-furan-2-one 
• 345319-67-7 (2Z,4Z)-Hepta-2,4-dienoic acid [3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10-methyl-5-oxo-4-triisopropylsilanyloxy-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-1-((2Z,4Z)-hepta-2,4-dienoylamino)-propyl]-amide 
• 345319-68-8 (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10-methyl-5-oxo-4-triisopropylsilanyloxy-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide 
• 345319-71-3 (2Z,4Z)-Hepta-2,4-dienoic acid {(Z)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10-methyl-5-oxo-4-triisopropylsilanyloxy-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide 
• 345319-69-9 (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide 
• 345319-72-4 (2Z,4Z)-Hepta-2,4-dienoic acid {(Z)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide 
• 345319-61-1 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester 
• 345319-66-6 (E)-(7R,9S,10R)-3-[9-(tert-butyldiphenylsilanyloxy)-10-methyl-5-oxo-4-(triisopropylsilanyloxy)-7,8,9,10,11,14-hexahydro-5H-6-oxabenzocyclododecen-7-yl]propionaldehyde 
• 345319-62-2 (E)-(7R,9S,10R)-7-(3-Benzyloxy-propyl)-9-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one 
• 345319-63-3 (E)-(7R,9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-7-(3-hydroxy-propyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one 

Relevant academic research and scientific papers

Stereoselective synthesis of a key intermediate of (-)-apicularen A

Progress towards the stereoselective formal synthesis of (-)-apicularen A is described. The convergent approach involves the assembly of aliphatic and aromatic fragments via Grubbs's cross metathesis. Other key reactions in the strategy include Sharpless

Synthesis of rimocidinolide methyl ester, the aglycone of (+)-rimocidin

An efficient, convergent route based on cyanohydrin acetonide couplings was used for the synthesis of the aglycone of rimocidin, rimocidinolide methyl ester (1). Cyanohydrin acetonides were used as β-hydroxyketone synthetic equivalents in the assembly of the polyol chain.

A convergent total synthesis of (-)-mucocin: An acetogenin from Annonaceae

A total synthesis of the Annonaceous acetogenin mucocin has been accomplished. The synthesis follows a convergent strategy, wherein at a very late stage the left part of the molecule is connected with the right part. The key reaction is the stereocontrolled addition of an organomagnesium compound 2 to the aldehyde 3. The THP ring of mucocin is build by a 6-endo epoxide cyclization of an epoxyacetonide precursor (16 → 17). The new modular synthetic approach developed herein should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogues.

Total synthesis of (-)-mucocin

A highly convergent, modular strategy for the total synthesis of the annonaceous acetogenin (-)-mucocin is reported. The remarkable features are the endoselective formation of the tetrahydropyran ring from an activated epoxide and the stability of the but

γ-Butyrolactone, an Alternative Source of Chiral Iodo Derivatives.

An efficient synthesis of (3S) 1,3-di-tert-butyldimethylsilyloxy-6-iodohexane, a chiral iodo derivative useful for the preparation of functionalised 1,7-dioxaspiroundecanes from γ-butyrolactone is described.

REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES

Red-Al reduction of allyl-alcohol epoxides was shown to yield 1,3-diols in high regioselectivity, while DIBAL reduction was shown to yield 1,2-diols.