A Kiyooka Aldol Approach for the Synthesis of the C(14)-C(23) Segment of the Diastereomeric Analog of Tedanolide C

作者：Buelow Leila; Naini Arun; Fohrer Joerg; Kalesse Markus^*

来源：Organic Letters, 2011, 13(22): 6038-6041.

DOI：10.1021/ol202515x

The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.

• 出版日期2011-11-18