Synlett 2004(8): 1359-1362  
DOI: 10.1055/s-2004-825619
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Ian Paterson*, Angela C. Mackay
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK
Fax: +44(1223)336362; e-Mail: ip100@cam.ac.uk;
Further Information

Publication History

Received 5 March 2004
Publication Date:
04 June 2004 (online)

Zoom Image

Abstract

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