Synthesis of the C29-C37 segment of spongistatin 1

Authors
Dunkel, R Treu, J Hoffmann, HMR
Citation
R. Dunkel et al., Synthesis of the C29-C37 segment of spongistatin 1, TETRAHEDR-A, 10(8), 1999, pp. 1539-1549
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
8
Year of publication
1999
Pages
1539 - 1549
Database
ISI
SICI code
0957-4166(19990423)10:8<1539:SOTCSO>2.0.ZU;2-V
Abstract
Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stere ogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-di ol sequence completes our methodology to all stereoisomers of 3,5,7-trihydr oxy heptanoic ester building blocks functionalized for alpha-oxyanion chemi stry. (C) 1999 Elsevier Science Ltd. All rights reserved.