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

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

20 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 UN Sustainable Development Goals (SDGs)

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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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DO - 10.1016/j.tet.2011.02.061

M3 - Article

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VL - 67

SP - 2882

EP - 2888

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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ER -

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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