Total synthesis of (±)-dragmacidin e

Ken S. Feldman, Paiboon Ngernmeesri

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The bis indole sponge alkaloid dragmacidin E was synthesized in racemic form over 25 steps starting from 7-benzhydroxyindole. Key steps include (a) a Witkop cyclization to facilitate construction of the indole-spanning seven-membered ring and (b) a cyclodehydrative pyrazinone synthesis that unites the two indole-containing sectors.

Original languageEnglish (US)
Pages (from-to)5704-5707
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
StatePublished - Oct 21 2011

Fingerprint

indoles
Indole Alkaloids
Porifera
Cyclization
synthesis
alkaloids
Alkaloids
sectors
rings
indole
dragmacidin E

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Feldman, K. S., & Ngernmeesri, P. (2011). Total synthesis of (±)-dragmacidin e. Organic Letters, 13(20), 5704-5707. https://doi.org/10.1021/ol202535f
Feldman, Ken S. ; Ngernmeesri, Paiboon. / Total synthesis of (±)-dragmacidin e. In: Organic Letters. 2011 ; Vol. 13, No. 20. pp. 5704-5707.
@article{32274cb36d60424591c842fdba01d198,
title = "Total synthesis of (±)-dragmacidin e",
abstract = "The bis indole sponge alkaloid dragmacidin E was synthesized in racemic form over 25 steps starting from 7-benzhydroxyindole. Key steps include (a) a Witkop cyclization to facilitate construction of the indole-spanning seven-membered ring and (b) a cyclodehydrative pyrazinone synthesis that unites the two indole-containing sectors.",
author = "Feldman, {Ken S.} and Paiboon Ngernmeesri",
year = "2011",
month = "10",
day = "21",
doi = "10.1021/ol202535f",
language = "English (US)",
volume = "13",
pages = "5704--5707",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "20",

}

Feldman, KS & Ngernmeesri, P 2011, 'Total synthesis of (±)-dragmacidin e', Organic Letters, vol. 13, no. 20, pp. 5704-5707. https://doi.org/10.1021/ol202535f

Total synthesis of (±)-dragmacidin e. / Feldman, Ken S.; Ngernmeesri, Paiboon.

In: Organic Letters, Vol. 13, No. 20, 21.10.2011, p. 5704-5707.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Total synthesis of (±)-dragmacidin e

AU - Feldman, Ken S.

AU - Ngernmeesri, Paiboon

PY - 2011/10/21

Y1 - 2011/10/21

N2 - The bis indole sponge alkaloid dragmacidin E was synthesized in racemic form over 25 steps starting from 7-benzhydroxyindole. Key steps include (a) a Witkop cyclization to facilitate construction of the indole-spanning seven-membered ring and (b) a cyclodehydrative pyrazinone synthesis that unites the two indole-containing sectors.

AB - The bis indole sponge alkaloid dragmacidin E was synthesized in racemic form over 25 steps starting from 7-benzhydroxyindole. Key steps include (a) a Witkop cyclization to facilitate construction of the indole-spanning seven-membered ring and (b) a cyclodehydrative pyrazinone synthesis that unites the two indole-containing sectors.

UR - http://www.scopus.com/inward/record.url?scp=80054689458&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054689458&partnerID=8YFLogxK

U2 - 10.1021/ol202535f

DO - 10.1021/ol202535f

M3 - Article

VL - 13

SP - 5704

EP - 5707

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

Feldman KS, Ngernmeesri P. Total synthesis of (±)-dragmacidin e. Organic Letters. 2011 Oct 21;13(20):5704-5707. https://doi.org/10.1021/ol202535f