Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition

T. J. Greshock; Raymond L. Funk

doi:10.1021/ol0165903

Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition

T. J. Greshock, Raymond L. Funk

Chemistry

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67 Scopus citations

Abstract

(matrix presented) The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.

Original language	English (US)
Pages (from-to)	3511-3514
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	22
DOIs	https://doi.org/10.1021/ol0165903
State	Published - Nov 1 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0165903

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abstract = "(matrix presented) The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.",

author = "Greshock, {T. J.} and Funk, {Raymond L.}",

year = "2001",

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doi = "10.1021/ol0165903",

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AU - Funk, Raymond L.

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N2 - (matrix presented) The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.

AB - (matrix presented) The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.

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Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition

Abstract

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