Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• 6a (Scheme 2) with correct absolute configurations for castanospermine (C-8/C-8a), we sought to transform 6a into the target alkaloid, and in this paper report on the synthesis of an advanced intermediate towards this goal. Thus, adduct 6a underwent oxidative cleavage of the PMB protecting group

Do α-acyloxy and α-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?

• Dennis P. Curran and
• Tiffany R. Turner

Beilstein J. Org. Chem. 2006, 2, No. 10, doi:10.1186/1860-5397-2-10

• -butenylmagnesium bromide to 3-methylcyclohexenone followed by quenching with either acetyl chloride [26] or methyl chloroformate provided enol ester 9a (50%) and enol carbonate 9b (83%). Oxidative cleavage [27][28][29] and reduction then provided alcohols 10a and 10b, which were converted to iodides 11a and 11b