Catalytic asymmetric synthesis of descurainin via 1, 3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4

Naoyuki Shimada; Taiki Hanari; Yasunobu Kurosaki; Masahiro Anada; Hisanori Nambu; Shunichi Hashimoto

doi:10.1016/j.tetlet.2010.10.036

Catalytic asymmetric synthesis of descurainin via 1, 3-dipolar cycloaddition of a carbonyl ylide using Rh₂(R-TCPTTL)₄

Naoyuki Shimada, Taiki Hanari, Yasunobu Kurosaki, Masahiro Anada, Hisanori Nambu, Shunichi Hashimoto^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

30 Scopus citations

Abstract

A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrogénation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl₅ as the key step. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3- oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh ₂(K-TCPTTL)₄, provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee.

Original language	English
Pages (from-to)	6572-6575
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2010.10.036
State	Published - 2010/12/15

Keywords

1-3-Dipolar cycloaddition
Carbonyl ylide
Chiral dirhodium(II) catalyst
Descurainin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.10.036

Cite this

@article{c2ca5ce2e0b84e0fa7cfaf249547284c,

title = "Catalytic asymmetric synthesis of descurainin via 1, 3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4",

abstract = "A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrog{\'e}nation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl5 as the key step. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3- oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh 2(K-TCPTTL)4, provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee.",

keywords = "1-3-Dipolar cycloaddition, Carbonyl ylide, Chiral dirhodium(II) catalyst, Descurainin",

author = "Naoyuki Shimada and Taiki Hanari and Yasunobu Kurosaki and Masahiro Anada and Hisanori Nambu and Shunichi Hashimoto",

note = "Funding Information: This research was supported, in part, by a Grant-in-Aid for Scientific Research on Innovative Areas (Project No. 2105: Organic Synthesis Based on Reaction Integration) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank S. Oka, M. Kiuchi and T. Hirose of the Center for Instrumental Analysis at Hokkaido University for mass measurements and elemental analysis. ",

year = "2010",

month = dec,

day = "15",

doi = "10.1016/j.tetlet.2010.10.036",

language = "英語",

volume = "51",

pages = "6572--6575",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "50",

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T1 - Catalytic asymmetric synthesis of descurainin via 1, 3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4

AU - Shimada, Naoyuki

AU - Hanari, Taiki

AU - Kurosaki, Yasunobu

AU - Anada, Masahiro

AU - Nambu, Hisanori

AU - Hashimoto, Shunichi

N1 - Funding Information: This research was supported, in part, by a Grant-in-Aid for Scientific Research on Innovative Areas (Project No. 2105: Organic Synthesis Based on Reaction Integration) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank S. Oka, M. Kiuchi and T. Hirose of the Center for Instrumental Analysis at Hokkaido University for mass measurements and elemental analysis.

PY - 2010/12/15

Y1 - 2010/12/15

N2 - A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrogénation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl5 as the key step. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3- oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh 2(K-TCPTTL)4, provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee.

AB - A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrogénation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl5 as the key step. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3- oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh 2(K-TCPTTL)4, provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee.

KW - 1-3-Dipolar cycloaddition

KW - Carbonyl ylide

KW - Chiral dirhodium(II) catalyst

KW - Descurainin

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DO - 10.1016/j.tetlet.2010.10.036

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