A Total Synthesis of the Marine Alkaloid Discoipyrrole D

Yiwen Zhang; Martin G. Banwell

doi:10.1021/acs.joc.7b01192

A Total Synthesis of the Marine Alkaloid Discoipyrrole D

Yiwen Zhang
, Martin G. Banwell^*

^*Corresponding author for this work

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

11 Citations (Scopus)

Abstract

A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.

Original language	English
Pages (from-to)	9328-9334
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.7b01192
Publication status	Published - 15 Sept 2017

Access to Document

10.1021/acs.joc.7b01192

Cite this

@article{c9e90ab236d7411e89ae112d85833c86,

title = "A Total Synthesis of the Marine Alkaloid Discoipyrrole D",

abstract = "A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.",

author = "Yiwen Zhang and Banwell, \{Martin G.\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = sep,

day = "15",

doi = "10.1021/acs.joc.7b01192",

language = "English",

volume = "82",

pages = "9328--9334",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - A Total Synthesis of the Marine Alkaloid Discoipyrrole D

AU - Zhang, Yiwen

AU - Banwell, Martin G.

PY - 2017/9/15

Y1 - 2017/9/15

N2 - A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.

AB - A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.

UR - https://www.scopus.com/pages/publications/85029539205

U2 - 10.1021/acs.joc.7b01192

DO - 10.1021/acs.joc.7b01192

M3 - Article

SN - 0022-3263

VL - 82

SP - 9328

EP - 9334

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

A Total Synthesis of the Marine Alkaloid Discoipyrrole D

Abstract

Access to Document

Other files and links

Fingerprint

Cite this