Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction

Porino Va; William R Roush

doi:10.1021/ol0628098

Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction

Org Lett. 2007 Jan 18;9(2):307-10. doi: 10.1021/ol0628098.

Authors

Porino Va¹, William R Roush

Affiliation

¹ Departments of Chemistry and Biochemistry, Scripps Florida, Jupiter, Florida 33458, USA.

Abstract

A synthesis of 2-epi-amphidinolide E (1) has been accomplished via an unexpected and highly diastereoselective C(2) stereochemical inversion during the modified Yamaguchi esterification of alcohol 4b and Fe(CO)3-complexed dienoic acid 7. [reaction: see text].

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Esterification
Molecular Conformation
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
amphidinolide E

Abstract

Publication types

MeSH terms

Substances

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