Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides

Yutaka Matsuda; Takayuki Koyama; Masaya Kato; Tomonori Kawaguchi; Yoko Saikawa; Masaya Nakata

doi:10.1016/j.tet.2015.02.037

Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides

Yutaka Matsuda, Takayuki Koyama, Masaya Kato, Tomonori Kawaguchi, Yoko Saikawa, Masaya Nakata

Department of Applied Chemistry

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

7 Citations (Scopus)

Abstract

5-exo-Dig versus 6-endo-dig oxycyclizations of alkynols having an internal triple bond catalyzed by PdCl₂, followed by methoxycarbonylation of the resulting vinylpalladium intermediates, are described. With an aim toward the total synthesis of polymaxenolides, a hybrid marine natural product containing a dihydropyran substructure, a model alkynol having the africane-type sesquiterpenoid skeleton was treated with PdCl₂ and 1,4-benzoquinone in MeOH under an atmosphere of CO (balloon) to afford the desired 6-endo-dig oxycyclization-methoxycarbonylation product.

Original language	English
Pages (from-to)	2134-2148
Number of pages	15
Journal	Tetrahedron
Volume	71
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2015.02.037
Publication status	Published - 2015 Apr 8

Keywords

5-exo-Dig
6-endo-Dig
Oxycyclization-methoxycarbonylation
Polymaxenolide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.tet.2015.02.037

Cite this

@article{689b20d0f97a48d2aa1026808972e634,

title = "Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides",

abstract = "5-exo-Dig versus 6-endo-dig oxycyclizations of alkynols having an internal triple bond catalyzed by PdCl2, followed by methoxycarbonylation of the resulting vinylpalladium intermediates, are described. With an aim toward the total synthesis of polymaxenolides, a hybrid marine natural product containing a dihydropyran substructure, a model alkynol having the africane-type sesquiterpenoid skeleton was treated with PdCl2 and 1,4-benzoquinone in MeOH under an atmosphere of CO (balloon) to afford the desired 6-endo-dig oxycyclization-methoxycarbonylation product.",

keywords = "5-exo-Dig, 6-endo-Dig, Oxycyclization-methoxycarbonylation, Polymaxenolide",

author = "Yutaka Matsuda and Takayuki Koyama and Masaya Kato and Tomonori Kawaguchi and Yoko Saikawa and Masaya Nakata",

note = "Funding Information: This research was partially supported by a {\textquoteleft}MEXT-Supported Program for the Strategic Research Foundation at Private Universities 2012–2016{\textquoteright}. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2015",

month = apr,

day = "8",

doi = "10.1016/j.tet.2015.02.037",

language = "English",

volume = "71",

pages = "2134--2148",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides

AU - Matsuda, Yutaka

AU - Koyama, Takayuki

AU - Kato, Masaya

AU - Kawaguchi, Tomonori

AU - Saikawa, Yoko

AU - Nakata, Masaya

N1 - Funding Information: This research was partially supported by a ‘MEXT-Supported Program for the Strategic Research Foundation at Private Universities 2012–2016’. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/4/8

Y1 - 2015/4/8

N2 - 5-exo-Dig versus 6-endo-dig oxycyclizations of alkynols having an internal triple bond catalyzed by PdCl2, followed by methoxycarbonylation of the resulting vinylpalladium intermediates, are described. With an aim toward the total synthesis of polymaxenolides, a hybrid marine natural product containing a dihydropyran substructure, a model alkynol having the africane-type sesquiterpenoid skeleton was treated with PdCl2 and 1,4-benzoquinone in MeOH under an atmosphere of CO (balloon) to afford the desired 6-endo-dig oxycyclization-methoxycarbonylation product.

AB - 5-exo-Dig versus 6-endo-dig oxycyclizations of alkynols having an internal triple bond catalyzed by PdCl2, followed by methoxycarbonylation of the resulting vinylpalladium intermediates, are described. With an aim toward the total synthesis of polymaxenolides, a hybrid marine natural product containing a dihydropyran substructure, a model alkynol having the africane-type sesquiterpenoid skeleton was treated with PdCl2 and 1,4-benzoquinone in MeOH under an atmosphere of CO (balloon) to afford the desired 6-endo-dig oxycyclization-methoxycarbonylation product.

KW - 5-exo-Dig

KW - 6-endo-Dig

KW - Oxycyclization-methoxycarbonylation

KW - Polymaxenolide

UR - http://www.scopus.com/inward/record.url?scp=84925533269&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84925533269&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2015.02.037

DO - 10.1016/j.tet.2015.02.037

M3 - Article

AN - SCOPUS:84925533269

SN - 0040-4020

VL - 71

SP - 2134

EP - 2148

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this