Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone

Maloy Nayak, Ikyon Kim

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.

Original languageEnglish
Pages (from-to)11460-11467
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number22
DOIs
Publication statusPublished - 2015 Nov 20

Fingerprint

Benzopyrans
Alkynes
Biological Products
deguelin
munduserone

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

@article{91f1b34cdb5f49338a748f73659443c5,
title = "Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone",
abstract = "A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.",
author = "Maloy Nayak and Ikyon Kim",
year = "2015",
month = "11",
day = "20",
doi = "10.1021/acs.joc.5b02160",
language = "English",
volume = "80",
pages = "11460--11467",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "22",

}

Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes : Syntheses of (±)-Deguelin and (±)-Munduserone. / Nayak, Maloy; Kim, Ikyon.

In: Journal of Organic Chemistry, Vol. 80, No. 22, 20.11.2015, p. 11460-11467.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes

T2 - Syntheses of (±)-Deguelin and (±)-Munduserone

AU - Nayak, Maloy

AU - Kim, Ikyon

PY - 2015/11/20

Y1 - 2015/11/20

N2 - A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.

AB - A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.

UR - http://www.scopus.com/inward/record.url?scp=84947968669&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84947968669&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b02160

DO - 10.1021/acs.joc.5b02160

M3 - Article

C2 - 26525067

AN - SCOPUS:84947968669

VL - 80

SP - 11460

EP - 11467

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 22

ER -