A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

The C 1′C 11′ portion of the antibiotic pamamycin-607 was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute co...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron: asymmetry Vol. 8; no. 21; pp. 3665 - 3673
Main Authors Mandville, Gérard, Girard, Christian, Bloch, Robert
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.11.1997
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
MYCELIUM-INDUCING SUBSTANCE
ANTIBIOTICS
REDUCTION
TETRAHYDROFURANS
STEREOCHEMISTRY
STREPTOMYCES-ALBONIGER
STEREOCONTROLLED SYNTHESIS
Online AccessGet full text

Cover

More Information
Summary:The C 1′C 11′ portion of the antibiotic pamamycin-607 was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C 6′ and C 8′ were fixed by an aldol condensation followed by an anti-reduction of the resulting β-hydroxyketone. The configurations of the last two asymmetric centers C 2′ and C 3′ were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(97)00475-8