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

48 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

Access to Document

10.1021/ol016850g

Cite this

@article{55e4fa7f3ab74fd4b0c47d3633dd3545,

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)",

volume = "4",

pages = "331--333",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0037034347&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037034347&partnerID=8YFLogxK

U2 - 10.1021/ol016850g

DO - 10.1021/ol016850g

M3 - Article

C2 - 11820872

AN - SCOPUS:0037034347

SN - 1523-7060

VL - 4

SP - 331

EP - 333

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this