88223-83-0

Upstream product

• 99838-72-9 (2R)-3-benzyloxy-1,2-epoxy-5-hexene 
• 925-90-6 ethylmagnesium bromide 
• 159622-96-5 (R)-(+)-2-Benzyloxypent-4-enal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 100-44-7 benzyl chloride 
• 88223-73-8 (2S,3S,4R)-4-Benzyloxy-hept-6-ene-2,3-diol 
• 85273-19-4 (2S,3S,4R)-2,3-isopropylidenedioxyhept-6-en-4-ol 
• 88223-75-0 Benzoic acid (1S,2S,3R)-3-benzyloxy-1-methyl-2-(toluene-4-sulfonyloxy)-hex-5-enyl ester 
• 88223-74-9 Benzoic acid (1S,2S,3R)-3-benzyloxy-2-hydroxy-1-methyl-hex-5-enyl ester 
• 236110-81-9 (4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one 
• 88223-82-9 (2R,3S)-2-((R)-1-Benzyloxy-but-3-enyl)-3-methyl-oxirane 

Downstream Products

• 253450-88-3 [(1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy]-acetic acid 
• 441018-95-7 2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester 
• 331414-52-9 (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester 
• 331414-64-3 (4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol 
• 331414-50-7 (2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-en-1-ol 
• 331414-51-8 (2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enal 
• 331414-49-4 (4R)-4-benzyl-3-[(2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enoyl]-oxazolidin-2-one 
• 289619-01-8 (4R)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one 
• 253450-80-5 (4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 253450-82-7 (4S)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one 
• 3442-58-8 (+)-laurencin 

Relevant academic research and scientific papers

An approach to lauroxanes by iterative use of Co2(CO) 6-acetylenic complexes. A formal synthesis of (+)-laurencin

A new approach to lauroxanes by a powerful and highly convergent methodology based on iterative use of Co2(CO)6-acetylenic complexes is described. The strategy employs an intermolecular Nicholas reaction to form unsaturated branched linear ethers, a ring closing metathesis to obtain the cobalt complex cyclic ethers, and an isomerization promoted by montmorillonite K-10. A short synthesis of cyclic ethers of seven-, eight-, and nine-membered rings is described. Additionally, the methodology is exemplified by the formal synthesis of (+)-laurencin, a red algae metabolite.

Ring closing metathesis for the formation of medium ring ethers: The total synthesis of (-)-isolaurallene

The total synthesis of the marine metabolite (-)-isolaurallene is described. Two approaches to the core nine-membered ether are presented both of which are based on a ring closing metathesis to close the cyclic ether.

Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers.

[formula: see text] The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.

Enantio- and Diastereocontrolled Synthesis of Chiral 1,2-Diol Derivatives from (R)-2,3-Di-O-isopropylideneglyceraldehyde: endo- and exo-Brevicomin

All four possible stereoisomers of the insect pheromone brevicomin have been prepared from (R)-2,3-di-O-isopropylideneglyceraldehyde (1) on stereocontrolled routes with ee more than 98-99percent.

CARBOHYDRATE-LIKE CHIRAL SYNTHONS. PREPARATION OF (R) γ-HEXENOLIDE, (5R,6S,7S) 6,7-ISOPROPYLIDENDIOXY-δ-OCTANOLIDE AND (+)-EXOBREVICOMIN FROM (2S,3S,4R) 2,3-ISOPROPYLIDENDIOXY-4-BENZYLOXYHEPT-6-ENE

The C6, C7, C8 and C9 chiral products (8), (7), (14) and (19), containing one, two and three oxygen-substituted chiral centres, respectively, have been prepared from the carbohydrate-like optically active, Csub