1,3-ASYMMETRIC INDUCTION IN ELECTROPHILIC ADDITION ONTO HOMOALLYLSILANES - AN APPROACH TOWARDS THE TOTAL SYNTHESIS OF (+ -)-KUMAUSYNE/

Authors
ANDREY O GLANZMANN C LANDAIS Y PARRARAPADO L
Citation
O. Andrey et al., 1,3-ASYMMETRIC INDUCTION IN ELECTROPHILIC ADDITION ONTO HOMOALLYLSILANES - AN APPROACH TOWARDS THE TOTAL SYNTHESIS OF (+ -)-KUMAUSYNE/, Tetrahedron, 53(8), 1997, pp. 2835-2854
Citations number
65
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
8
Year of publication
1997
Pages
2835 - 2854
Database
ISI
SICI code
0040-4020(1997)53:8<2835:1IIEAO>2.0.ZU;2-W
Abstract
Electrophilic 5-exo-trig cyclizations of homoallylsilanes have been ca rried out leading to 2,4- and 2,4,5-substituted tetrahydrofurans with good yields and diastereoselectivities. With disubstituted homoallylsi lanes, tetrahydrofurans having acyclic chiral centres were also obtain ed. An application of this methodology to an approach towards the tota l synthesis of (+/-)-kumausyne is proposed on the basis of these preli minary results. The four chiral centres of this marine natural product have been set up with excellent diastereoselectivities. (C) 1997 Else vier Science Ltd.