TOTAL SYNTHESIS AND STEREOCHEMISTRY OF 13-HYDROXY-ALPHA-EUDESMOL

Authors
CHEN YG XIONG ZM ZHOU G LIU LJ LI YL
Citation
Yg. Chen et al., TOTAL SYNTHESIS AND STEREOCHEMISTRY OF 13-HYDROXY-ALPHA-EUDESMOL, Tetrahedron : asymmetry, 9(11), 1998, pp. 1923-1928
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
11
Year of publication
1998
Pages
1923 - 1928
Database
ISI
SICI code
0957-4166(1998)9:11<1923:TSASO1>2.0.ZU;2-L
Abstract
The first total synthesis of both C-11 epimers of 13-hydroxy-alpha-eud esmol 1a and 1b by the use, as a key reaction, of the Sharpless asymme tric dihydroxylation of alkene 7 is presented. The absolute configurat ion of natural 13-hydroxy-alpha-eudesmol is established through compar ison of the H-1 NMR spectrum of natural diol and synthetic diols. In o ur synthesis another natural product (+)-alpha-selinene 2 has also bee n accomplished. (C) 1998 Elsevier Science Ltd. All rights reserved.