Total synthesis of brevenal

Hiroyoshi Takamura; Yuji Yamagami; Takayuki Kishi; Shigetoshi Kikuchi; Yuichi Nakamura; Isao Kadota; Yoshinori Yamamoto

doi:10.1016/j.tet.2010.05.069

Total synthesis of brevenal

Hiroyoshi Takamura, Yuji Yamagami, Takayuki Kishi, Shigetoshi Kikuchi, Yuichi Nakamura, Isao Kadota, Yoshinori Yamamoto

School of Science

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

19 Citations (Scopus)

Abstract

The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved.The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound.An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined.The right-and left-hand side chains were introduced by Wittig and HornereWadswortheEmmons reactions, respectively, to furnish brevenal (1).

Original language	English
Pages (from-to)	5329-5344
Number of pages	16
Journal	Tetrahedron
Volume	66
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2010.05.069
Publication status	Published - Jul 17 2010

Keywords

Brevenal
Intramolecular allylation
Marine polycyclic ether
Ring-closing metathesis
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.05.069

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title = "Total synthesis of brevenal",

abstract = "The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved.The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound.An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined.The right-and left-hand side chains were introduced by Wittig and HornereWadswortheEmmons reactions, respectively, to furnish brevenal (1).",

keywords = "Brevenal, Intramolecular allylation, Marine polycyclic ether, Ring-closing metathesis, Total synthesis",

author = "Hiroyoshi Takamura and Yuji Yamagami and Takayuki Kishi and Shigetoshi Kikuchi and Yuichi Nakamura and Isao Kadota and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Nagase Science and Technology Foundation , the Wesco Scientific Promotion Foundation , the Naito Foundation , the Sumitomo Foundation , and the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan . ",

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T1 - Total synthesis of brevenal

AU - Takamura, Hiroyoshi

AU - Yamagami, Yuji

AU - Kishi, Takayuki

AU - Kikuchi, Shigetoshi

AU - Nakamura, Yuichi

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Nagase Science and Technology Foundation , the Wesco Scientific Promotion Foundation , the Naito Foundation , the Sumitomo Foundation , and the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan .

PY - 2010/7/17

Y1 - 2010/7/17

N2 - The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved.The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound.An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined.The right-and left-hand side chains were introduced by Wittig and HornereWadswortheEmmons reactions, respectively, to furnish brevenal (1).

AB - The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved.The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound.An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined.The right-and left-hand side chains were introduced by Wittig and HornereWadswortheEmmons reactions, respectively, to furnish brevenal (1).

KW - Brevenal

KW - Intramolecular allylation

KW - Marine polycyclic ether

KW - Ring-closing metathesis

KW - Total synthesis

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DO - 10.1016/j.tet.2010.05.069

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VL - 66

SP - 5329

EP - 5344

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Total synthesis of brevenal

Abstract

Keywords

ASJC Scopus subject areas

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