Studies Towards the Synthesis of Superstolide A: An Aldol-Based Construction of an Advanced C1-C5/C20-C26 Segment

• DOI: 10.1055/s-2004-825619
• Publication Date: 2004-06-22T07:07:11Z
• Authors: Ian Paterson; Angela C. Mackay
• Keywords: Aldol reaction; Aldol condensation

Based on a boron-mediated syn aldol reaction of an alanine-derived ethyl ketone with α-chiral aldehyde partner, advanced intermediate for superstolide A was assembled in highly stereocontrolled fashion. Controlled 1,3-anti reduction the resulting β-hydroxy gave characteristic amino diol stereopentad superstolide, followed by Takai olefination and esterification C23 hydroxyl to provide elaborated C1-C5/C20-C26 segment 3.