Synthesis of the C1-C9 fragment of callipeltoside-A

Authors
Velazquez, F Olivo, HF
Citation
F. Velazquez et Hf. Olivo, Synthesis of the C1-C9 fragment of callipeltoside-A, ORG LETT, 2(13), 2000, pp. 1931-1933
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
13
Year of publication
2000
Pages
1931 - 1933
Database
ISI
SICI code
1523-7060(20000629)2:13<1931:SOTCFO>2.0.ZU;2-I
Abstract
The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselec tive epoxidation and further regiocontrolled nucleophilic opening of the ox irane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.