Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization

Miyu Furuta, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton.

Original languageEnglish
Pages (from-to)2316-2322
Number of pages7
JournalTetrahedron
Volume73
Issue number16
DOIs
Publication statusPublished - 2017 Apr 20

Fingerprint

Limonins
Cyclization
Skeleton
Bioactivity
Esters

Keywords

  • Domino cyclization
  • Limonoid
  • Radical cyclization
  • Stereoselective
  • Tetracyclic core

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization. / Furuta, Miyu; Hanaya, Kengo; Sugai, Takeshi; Shoji, Mitsuru.

In: Tetrahedron, Vol. 73, No. 16, 20.04.2017, p. 2316-2322.

Research output: Contribution to journalArticle

@article{337cdb143f52455aafc1018bac19bd63,
title = "Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization",
abstract = "Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton.",
keywords = "Domino cyclization, Limonoid, Radical cyclization, Stereoselective, Tetracyclic core",
author = "Miyu Furuta and Kengo Hanaya and Takeshi Sugai and Mitsuru Shoji",
year = "2017",
month = "4",
day = "20",
doi = "10.1016/j.tet.2017.03.021",
language = "English",
volume = "73",
pages = "2316--2322",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization

AU - Furuta, Miyu

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Shoji, Mitsuru

PY - 2017/4/20

Y1 - 2017/4/20

N2 - Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton.

AB - Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton.

KW - Domino cyclization

KW - Limonoid

KW - Radical cyclization

KW - Stereoselective

KW - Tetracyclic core

UR - http://www.scopus.com/inward/record.url?scp=85015043795&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85015043795&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.03.021

DO - 10.1016/j.tet.2017.03.021

M3 - Article

AN - SCOPUS:85015043795

VL - 73

SP - 2316

EP - 2322

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 16

ER -