Total synthesis of tryprostatins A and B

Takayuki Yamakawa; Eiji Ideue; Yuzo Iwaki; Ayumu Sato; Hidetoshi Tokuyama; Jun Shimokawa; Tohru Fukuyama

doi:10.1016/j.tet.2011.05.112

Total synthesis of tryprostatins A and B

Takayuki Yamakawa, Eiji Ideue, Yuzo Iwaki, Ayumu Sato, Hidetoshi Tokuyama, Jun Shimokawa, Tohru Fukuyama

PHA - Molecular Pharmaceutical Science

The University of Tokyo

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

24 Citations (Scopus)

Abstract

Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

Original language	English
Pages (from-to)	6547-6560
Number of pages	14
Journal	Tetrahedron
Volume	67
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2011.05.112
Publication status	Published - 2011 Sept 2

Keywords

Alkaloids
Natural product
Radical cyclization
Total Synthesis

Access to Document

10.1016/j.tet.2011.05.112

Cite this

@article{a919f4c2f29a4429946f6ef92f2e1883,

title = "Total synthesis of tryprostatins A and B",

abstract = "Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, F{\"u}rstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.",

keywords = "Alkaloids, Natural product, Radical cyclization, Total Synthesis",

author = "Takayuki Yamakawa and Eiji Ideue and Yuzo Iwaki and Ayumu Sato and Hidetoshi Tokuyama and Jun Shimokawa and Tohru Fukuyama",

note = "Funding Information: Financial support for this research was provided by Grants-in-Aid ( 21790009 and 20002004 ) from the Ministry of Education, Culture, Sports, Science and Technology of Japan. ",

year = "2011",

month = sep,

day = "2",

doi = "10.1016/j.tet.2011.05.112",

language = "English",

volume = "67",

pages = "6547--6560",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "35",

}

TY - JOUR

T1 - Total synthesis of tryprostatins A and B

AU - Yamakawa, Takayuki

AU - Ideue, Eiji

AU - Iwaki, Yuzo

AU - Sato, Ayumu

AU - Tokuyama, Hidetoshi

AU - Shimokawa, Jun

AU - Fukuyama, Tohru

N1 - Funding Information: Financial support for this research was provided by Grants-in-Aid ( 21790009 and 20002004 ) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

PY - 2011/9/2

Y1 - 2011/9/2

N2 - Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

AB - Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

KW - Alkaloids

KW - Natural product

KW - Radical cyclization

KW - Total Synthesis

UR - http://www.scopus.com/inward/record.url?scp=79960946901&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960946901&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2011.05.112

DO - 10.1016/j.tet.2011.05.112

M3 - Article

AN - SCOPUS:79960946901

SN - 0040-4020

VL - 67

SP - 6547

EP - 6560

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Total synthesis of tryprostatins A and B

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this