A concise synthesis of the octalactins.

The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearran...

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Xehetasun bibliografikoak
Egile Nagusiak: O'Sullivan, P, Buhr, W, Fuhry, M, Harrison, JR, Davies, J, Feeder, N, Marshall, DR, Burton, J, Holmes, AB
Formatua: Journal article
Hizkuntza:English
Argitaratua: 2004
Deskribapena
Gaia:The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.