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

Miyu Furuta; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji

doi:10.1016/j.tet.2017.03.021

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

Miyu Furuta, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

School of Pharmaceutical Sciences

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

8 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 language	English
Pages (from-to)	2316-2322
Number of pages	7
Journal	Tetrahedron
Volume	73
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2017.03.021
Publication status	Published - 2017

Keywords

Domino cyclization
Limonoid
Radical cyclization
Stereoselective
Tetracyclic core

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.03.021

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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",

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year = "2017",

doi = "10.1016/j.tet.2017.03.021",

language = "English",

volume = "73",

pages = "2316--2322",

journal = "Tetrahedron",

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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

Y1 - 2017

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

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DO - 10.1016/j.tet.2017.03.021

M3 - Article

AN - SCOPUS:85015043795

SN - 0040-4020

VL - 73

SP - 2316

EP - 2322

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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