STUDIES IN MARINE MACROLIDE SYNTHESIS - STEREOCONTROLLED SYNTHESIS OFTHE F-RING SUBUNIT OF SPONGISTATIN-1 (ALTOHYRTIN-A)

Authors
PATERSON I KEOWN LE
Citation
I. Paterson et Le. Keown, STUDIES IN MARINE MACROLIDE SYNTHESIS - STEREOCONTROLLED SYNTHESIS OFTHE F-RING SUBUNIT OF SPONGISTATIN-1 (ALTOHYRTIN-A), Tetrahedron letters, 38(32), 1997, pp. 5727-5730
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
32
Year of publication
1997
Pages
5727 - 5730
Database
ISI
SICI code
0040-4039(1997)38:32<5727:SIMMS->2.0.ZU;2-B
Abstract
The C-36-C-46 subunit 3, containing the F ring of spongistatin 1 (1), was prepared in 12 steps from ketone (R)-7. Key steps include: (i) the boron-mediated anti aldol reaction, 7 --> 9; (ii) the Sharpless AD, 6 --> 13; and(iii) an intramolecular hetero-Michael addition, followed by base-promoted equilibration to give 3. (C) 1997 Elsevier Science Lt d.