Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

Tomohiro Nagasawa; Tomoo Nukada; Shigefumi Kuwahara

doi:10.1016/j.tet.2011.02.061

Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

Tomohiro Nagasawa, Tomoo Nukada, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

19 Citations (Scopus)

Abstract

The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.

Original language	English
Pages (from-to)	2882-2888
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2011.02.061
Publication status	Published - 2011 Apr 22

Keywords

Aspergillide
Cytotoxic
Isomerization
Macrolide
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following Sustainable Development Goal(s)

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10.1016/j.tet.2011.02.061

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title = "Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran",

abstract = "The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.",

keywords = "Aspergillide, Cytotoxic, Isomerization, Macrolide, Total synthesis",

author = "Tomohiro Nagasawa and Tomoo Nukada and Shigefumi Kuwahara",

note = "Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology , Japan (No. 22380064 ). ",

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T1 - Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

AU - Nagasawa, Tomohiro

AU - Nukada, Tomoo

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology , Japan (No. 22380064 ).

PY - 2011/4/22

Y1 - 2011/4/22

N2 - The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.

AB - The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.

KW - Aspergillide

KW - Cytotoxic

KW - Isomerization

KW - Macrolide

KW - Total synthesis

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EP - 2888

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Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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