Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition

Jun Ho Maeng; Raymond L. Funk

doi:10.1021/ol015506g

Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition

Jun Ho Maeng, Raymond L. Funk

Chemistry

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

72 Scopus citations

Abstract

Matrix presented The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.

Original language	English (US)
Pages (from-to)	1125-1128
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	8
DOIs	https://doi.org/10.1021/ol015506g
State	Published - Apr 19 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol015506g

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abstract = "Matrix presented The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.",

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AB - Matrix presented The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.

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Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition

Abstract

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