253450-88-3

Upstream product

• 88223-83-0 (3R,4R)-4-benzyloxy-hept-6-en-3-ol 
• 79-08-3 bromoacetic acid 
• 236110-81-9 (4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one 
• 159622-96-5 (R)-(+)-2-Benzyloxypent-4-enal 

Downstream Products

• 289900-49-8 (4R)-4-Benzyl-3-[(2S)-2-((1R,2R)-2-benzyloxy-1-ethylpent-4-enyloxy)pent-4-enoyl]oxazolidin-2-one 
• 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

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.