Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment

Craig E Stivala; Armen Zakarian

doi:10.1021/ol8027797

Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment

Org Lett. 2009 Feb 19;11(4):839-42. doi: 10.1021/ol8027797.

Authors

Craig E Stivala¹, Armen Zakarian

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Aldehydes / chemistry*
Catalysis
Lithium / chemistry
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Aldehydes
Spiro Compounds
spirolide C
3-hydroxybutanal
Lithium

Abstract

Publication types

MeSH terms

Substances

Grants and funding