Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

Michael A. Evans; Joshua R. Sacher; Steven M. Weinreb

doi:10.1016/j.tet.2008.10.060

Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

Michael A. Evans
, Joshua R. Sacher
, Steven M. Weinreb

Chemistry

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

28 Scopus citations

Abstract

A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.

Original language	English (US)
Pages (from-to)	6712-6719
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2008.10.060
State	Published - Aug 15 2009

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.10.060

Cite this

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title = "Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine",

abstract = "A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.",

author = "Evans, \{Michael A.\} and Sacher, \{Joshua R.\} and Weinreb, \{Steven M.\}",

note = "Funding Information: We gratefully acknowledge financial support from the National Institutes of Health (CA-034303). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Cystallographic Facility) for the X-ray determination of compound 22 , Jae Hong Seo for helpful discussions, and Ilia Korboukh for assistance in preparation of the manuscript.",

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T1 - Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

AU - Evans, Michael A.

AU - Sacher, Joshua R.

AU - Weinreb, Steven M.

N1 - Funding Information: We gratefully acknowledge financial support from the National Institutes of Health (CA-034303). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Cystallographic Facility) for the X-ray determination of compound 22 , Jae Hong Seo for helpful discussions, and Ilia Korboukh for assistance in preparation of the manuscript.

PY - 2009/8/15

Y1 - 2009/8/15

N2 - A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.

AB - A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.

UR - https://www.scopus.com/pages/publications/67650254222

UR - https://www.scopus.com/pages/publications/67650254222#tab=citedBy

U2 - 10.1016/j.tet.2008.10.060

DO - 10.1016/j.tet.2008.10.060

M3 - Article

AN - SCOPUS:67650254222

SN - 0040-4020

VL - 65

SP - 6712

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JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

Abstract

UN SDGs

All Science Journal Classification (ASJC) codes

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