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...

Полное описание

Библиографические подробности
Главные авторы: O'Sullivan, P, Buhr, W, Fuhry, M, Harrison, JR, Davies, J, Feeder, N, Marshall, DR, Burton, J, Holmes, AB
Формат: Journal article
Язык:English
Опубликовано: 2004
Описание
Итог: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.