Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.
A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy.
Stivala
Craig E
CE
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
Zakarian
Armen
A
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D013141:Spiro Compounds; C429216:spirolide C; C116609:3-hydroxybutanal; D008094:Lithium