Total synthesis of (±)-fasicularin via a 2-amidoacrolein cycloaddition

Jun Ho Maeng, Raymond L. Funk

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

(Equation Presented) The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.

Original languageEnglish (US)
Pages (from-to)331-333
Number of pages3
JournalOrganic Letters
Volume4
Issue number3
DOIs
StatePublished - Feb 7 2002

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Acrolein
Stereochemistry
Cycloaddition
Cytotoxins
Cycloaddition Reaction
stereochemistry
cycloaddition
Hydrides
hydrides
Ions
rings
synthesis
ions
formal glycol
fasicularin
3-hydroxybutanal
2-amidoacrolein

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "(Equation Presented) The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.",
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Total synthesis of (±)-fasicularin via a 2-amidoacrolein cycloaddition. / Maeng, Jun Ho; Funk, Raymond L.

In: Organic Letters, Vol. 4, No. 3, 07.02.2002, p. 331-333.

Research output: Contribution to journalArticle

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AB - (Equation Presented) The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.

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