ASYMMETRIC-SYNTHESIS OF (-)-DENTICULATIN-A AND (-)-DENTICULATIN-B VIAGROUP-SELECTIVE ALDOLIZATION OF A MESO DIALDEHYDE WITH A CHIRAL N-PROPIONYLSULTAM

Authors
OPPOLZER W DEBRABANDER J WALTHER E BERNARDINELLI G
Citation
W. Oppolzer et al., ASYMMETRIC-SYNTHESIS OF (-)-DENTICULATIN-A AND (-)-DENTICULATIN-B VIAGROUP-SELECTIVE ALDOLIZATION OF A MESO DIALDEHYDE WITH A CHIRAL N-PROPIONYLSULTAM, Tetrahedron letters, 36(25), 1995, pp. 4413-4416
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
25
Year of publication
1995
Pages
4413 - 4416
Database
ISI
SICI code
0040-4039(1995)36:25<4413:AO(A(V>2.0.ZU;2-G
Abstract
Aldolization of meso dialdehyde 3 with a borylenolate obtained from ch iral N-propionylsultam 4 yields efficiently lactols 5 with simultaneou s generation of five stereogenic centers. Dithioketalization/O-desilyl ation of 5 affords acyclic diol 9 which is converted into the marine p olypropionates 1a and 1b via the asymmetric alkylation of N-propionylt oluenesultam 11 and the aldol coupling 10 + 15 --> 16.