Oxabicyclo[3.2.1]octenes in organic synthesis - Direct ring opening of oxabicyclo[3.2.1] systems employing silyl ketene acetals in concentrated solutions of lithium perchlorate-diethyl ether: Application to the synthesis of the C(19)-C(27) fragment of rifamycin S

Authors
Hunt, KW Grieco, PA
Citation
Kw. Hunt et Pa. Grieco, Oxabicyclo[3.2.1]octenes in organic synthesis - Direct ring opening of oxabicyclo[3.2.1] systems employing silyl ketene acetals in concentrated solutions of lithium perchlorate-diethyl ether: Application to the synthesis of the C(19)-C(27) fragment of rifamycin S, ORG LETT, 3(3), 2001, pp. 481-484
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
481 - 484
Database
ISI
SICI code
1523-7060(20010208)3:3<481:OIOS-D>2.0.ZU;2-K
Abstract
[GRAPHICS] The direct opening at the bridgehead of oxabicyclo[3.2.1]octenes employing silyl ketene acetals in 4.0-5.0 M lithium perchlorate in diethyl ether has been realized, which gives rise to highly functionalized cycloheptadienes t hat can be further manipulated for use in natural product synthesis. The br idgehead opening reaction has been employed in the construction of the C(19 )-C(27) fragment of Rifamycin S.