Synthesis of (+)-casuarine

Scott E. Denmark; Alexander R. Hurd

doi:10.1021/jo991680v

Synthesis of (+)-casuarine

Scott E. Denmark, Alexander R. Hurd

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.

Original language	English (US)
Pages (from-to)	2875-2886
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	65
Issue number	10
DOIs	https://doi.org/10.1021/jo991680v
State	Published - May 19 2000

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo991680v

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AB - The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.

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Synthesis of (+)-casuarine

Abstract

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