558459-28-2

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 159622-96-5 (R)-(+)-2-Benzyloxypent-4-enal 
• 924-41-4 1,5-hexadiene-3-ol 
• 558459-27-1 (1R)-1-[(1S)-oxiranyl]-but-3-en-1-ol 
• 69831-70-5 (2R)-2-benzyloxy-pent-4-en-1-ol 
• 253450-86-1 (4S)-4-benzyl-3-[(2R)-2-benzyloxy-pent-4-enoyl]-oxazolidin-2-one 
• 236110-81-9 (4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one 

Downstream Products

• 558459-29-3 [(1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy]-acetic acid 
• 558459-43-1 (2S,3R,8R,9S)-8-benzyloxy-2-[2-(tert-butyl-diphenyl-silanyloxy)ethyl]-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol 
• 558459-44-2 [2-((2S,3S,8R,9S)-8-benzyloxy-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-ethoxy]-tert-butyl-diphenyl-silane 
• 558459-46-4 1-[(2S,3R,8R,9S)-3-(tert-butyldimethyl-silanyloxy)-9-ethyl-8-benzyloxy-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-3-methylbutane-2,3-diol 
• 558459-39-5 {(1R)-1-[(1S)-1-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-2-(3,3-dimethyloxiranyl)-ethyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane 
• 558459-33-9 [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane 
• 558459-25-9 [(1R,2S)-1-allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-methyl-hex-4-enyloxy]-tert-butyl-dimethyl-silane 
• 558459-35-1 3-[2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-(2S)-5-methyl-hex-4-enoyl]-(4R)-4-isopropyl-oxazolidin-2-one 
• 558459-30-6 (R)-3-[(Z)-(S)-2-((1S,2R)-2-Benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one 
• 558459-40-8 [(2S,3R,8R,9S)-8-benzyloxy-2-(3,3-dimethyl-oxiranylmethyl)-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane 
• 558459-41-9 [(2S,3R,8R,9S)-8-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-ethanol 
• 558459-58-8 [(2S,3R,8R,9S)-8-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-acetaldehyde 
• 558459-32-8 (Z)-(4R,5S)-5-((1S,2R)-2-Benzyloxy-1-ethyl-pent-4-enyloxy)-8-bromo-octa-1,7-dien-4-ol 
• 558459-37-3 5-[(1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy]-(4R,5S)-8-methyl-nona-1,7-dien-4-ol 

Relevant academic research and scientific papers

Enantioselective total synthesis of (+)-obtusenyne

A total synthesis of the laurencia metabolite (+)-obtusenyne has been completed. The key steps include a Sharpless kinetic resolution and an asymmetric glycolate alkylation to establish the stereogenic centers adjacent to the ether linkage and a ring-clos

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.