Asymmetric Syntheses of APTO and AETD: the beta-Amino Acid Fragments within Microsclerodermins C, D, and E

作者：Davies Stephen G^*; Fletcher Ai M; Foster Emma M; Lee James A; Roberts Paul M; Thomson James E

来源：Journal of Organic Chemistry, 2013, 78(6): 2500-2510.

DOI：10.1021/jo302731m

Efficient asymmetric syntheses of APTO and AETD, the highly functionalized beta-amino acid fragments within microsclerodermins C, D, and E, are reported. The conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to tert-butyl (E,E)-7-(triisopropylsilyloxy)hepta-2,4-dienoate and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine, diastereoselective dihydroxylation of a 2,3-syn-gamma,delta-unsaturated-alpha-hydroxy-beta-amino ester derivative under Donohoe conditions, and a Julia-Kocienski olefination were used as the key steps.

• 出版日期2013-3-15