A KETAL CLAISEN REARRANGEMENT FOR ALPHA-KETOL ISOPRENE UNIT ELONGATION - APPLICATION TO A PRACTICAL SYNTHESIS OF SARCOPHYTOL-A INTERMEDIATE

Authors
TAKAYANAGI H SUGIYAMA S MORINAKA Y
Citation
H. Takayanagi et al., A KETAL CLAISEN REARRANGEMENT FOR ALPHA-KETOL ISOPRENE UNIT ELONGATION - APPLICATION TO A PRACTICAL SYNTHESIS OF SARCOPHYTOL-A INTERMEDIATE, Journal of the Chemical Society. Perkin transactions. I, (7), 1995, pp. 751-756
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
7
Year of publication
1995
Pages
751 - 756
Database
ISI
SICI code
0300-922X(1995):7<751:AKCRFA>2.0.ZU;2-V
Abstract
A new ketal Claisen rearrangement using the ketal 10 for the isoprene unit elongation which affords terminal alpha-ketol terpenoid is presen ted. Its efficiency is demonstrated by successful transformation of th e product of this reaction, the alpha-ketol 20, into 2, the acyclic pr ecursor of sarcophytol A total synthesis, by two alternative routes vi a the beta,gamma-unsaturated aldehyde 24 and the allylic alcohol 28.