69831-70-5Relevant academic research and scientific papers
Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes
Chernega, Alexander N.,Davies, Stephen G.,Fletcher, Ai M.,Goodwin, Christopher J.,Hepworth, David,Prasad, R. Shyam,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Thomson, James E.
scheme or table, p. 4167 - 4194 (2010/07/06)
Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates α-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH4 to give enantiopure α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes in good yield.
Enantioselective synthesis of apoptolidinone: Exploiting the versatility of thiazolidinethione chiral auxiliaries
Crimmins, Michael T.,Christie, Hamish S.,Chaudhary, Kleem,Long, Alan
, p. 13810 - 13812 (2007/10/03)
An efficient, enantioselective synthesis of apoptolidinone has been completed, demonstrating the versatility of thiazolidinethione auxiliaries. Three propionate aldol additions and two asymmetric glycolate alkylations function to establish 8 of the 12 ste
Ring closing metathesis for the formation of medium ring ethers: The total synthesis of (-)-isolaurallene
Crimmins, Michael T,Emmitte, Kyle A,Choy, Allison L
, p. 1817 - 1834 (2007/10/03)
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.
Crimmins,Emmitte
, p. 2029 - 2032 (2008/02/11)
[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.
