An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

Aki Kohyama; Naoki Kanoh; Eunsang Kwon; Yoshiharu Iwabuchi

doi:10.1016/j.tetlet.2015.12.049

An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

Aki Kohyama, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

Tohoku University

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

10 Citations (Scopus)

Abstract

The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.

Original language	English
Pages (from-to)	517-519
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2015.12.049
Publication status	Published - 2016 Feb 3

Keywords

Epoxide ring opening
Fusarisetin A
Oxidative lactonization
Yamamoto asymmetric epoxidation

Access to Document

10.1016/j.tetlet.2015.12.049

Cite this

@article{b074e2e276a64f7fbb401eb71ced9c22,

title = "An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A",

abstract = "The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.",

keywords = "Epoxide ring opening, Fusarisetin A, Oxidative lactonization, Yamamoto asymmetric epoxidation",

author = "Aki Kohyama and Naoki Kanoh and Eunsang Kwon and Yoshiharu Iwabuchi",

note = "Funding Information: This research is partially supported by the Platform Project for Supporting in Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from Japan Agency for Medical Research and Development , and Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Advanced Molecular Transformations by Organocatalysts{\textquoteright} from MEXT , Japan, by a Grant-in-Aid for Scientific Research (B) (No. 24390001 ) from JSPS . Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2016",

month = feb,

day = "3",

doi = "10.1016/j.tetlet.2015.12.049",

language = "English",

volume = "57",

pages = "517--519",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "5",

}

TY - JOUR

T1 - An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

AU - Kohyama, Aki

AU - Kanoh, Naoki

AU - Kwon, Eunsang

AU - Iwabuchi, Yoshiharu

N1 - Funding Information: This research is partially supported by the Platform Project for Supporting in Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from Japan Agency for Medical Research and Development , and Grant-in-Aid for Scientific Research on Innovative Areas ‘Advanced Molecular Transformations by Organocatalysts’ from MEXT , Japan, by a Grant-in-Aid for Scientific Research (B) (No. 24390001 ) from JSPS . Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2016/2/3

Y1 - 2016/2/3

N2 - The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.

AB - The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.

KW - Epoxide ring opening

KW - Fusarisetin A

KW - Oxidative lactonization

KW - Yamamoto asymmetric epoxidation

UR - http://www.scopus.com/inward/record.url?scp=84954397100&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84954397100&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.12.049

DO - 10.1016/j.tetlet.2015.12.049

M3 - Article

AN - SCOPUS:84954397100

SN - 0040-4039

VL - 57

SP - 517

EP - 519

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this