Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition

Authors
Maeng, JH Funk, RL
Citation
Jh. Maeng et Rl. Funk, Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition, ORG LETT, 3(8), 2001, pp. 1125-1128
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
8
Year of publication
2001
Pages
1125 - 1128
Database
ISI
SICI code
1523-7060(20010419)3:8<1125:TSOTIF>2.0.ZU;2-M
Abstract
The total synthesis of the potent immunosuppressant FR901483 is described, In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacro lein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyc lohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deli ver the tricyclic ring system of the natural product, suitably functionaliz ed for completion of the total synthesis.