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

Jun Ho Maeng; Raymond L. Funk

doi:10.1021/ol016850g

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

Jun Ho Maeng
, Raymond L. Funk

Chemistry

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

51 Scopus citations

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 language	English (US)
Pages (from-to)	331-333
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	3
DOIs	https://doi.org/10.1021/ol016850g
State	Published - Feb 7 2002

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016850g

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title = "Total synthesis of (±)-fasicularin via a 2-amidoacrolein cycloaddition",

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.",

author = "Maeng, \{Jun Ho\} and Funk, \{Raymond L.\}",

year = "2002",

month = feb,

day = "7",

doi = "10.1021/ol016850g",

language = "English (US)",

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journal = "Organic Letters",

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T1 - Total synthesis of (±)-fasicularin via a 2-amidoacrolein cycloaddition

AU - Maeng, Jun Ho

AU - Funk, Raymond L.

PY - 2002/2/7

Y1 - 2002/2/7

N2 - (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.

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.

UR - https://www.scopus.com/pages/publications/0037034347

UR - https://www.scopus.com/pages/publications/0037034347#tab=citedBy

U2 - 10.1021/ol016850g

DO - 10.1021/ol016850g

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SN - 1523-7060

VL - 4

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EP - 333

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

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

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