Synthesis of the J ring segment of gambieric acid

Isao Kadota; Hiroyoshi Takamura; Yoshinori Yamamoto

doi:10.1016/S0040-4039(01)00530-5

Synthesis of the J ring segment of gambieric acid

Isao Kadota, Hiroyoshi Takamura, Yoshinori Yamamoto

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

31 Citations (Scopus)

Abstract

The J ring segment 2 of gambieric acid was synthesized stereoselectively by the coupling between the cyclic ether component 3 and the alkenyl iodide 4. The tetrahydropyran 3 was stereoselectively synthesized by the 6-endo-cyclization of a hydroxyepoxide prepared from deoxy-D-ribose. The side chain moiety 4 was prepared by the stereoselective hydrostannation of an internal alkyne.

Original language	English
Pages (from-to)	3649-3651
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(01)00530-5
Publication status	Published - May 21 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00530-5

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title = "Synthesis of the J ring segment of gambieric acid",

abstract = "The J ring segment 2 of gambieric acid was synthesized stereoselectively by the coupling between the cyclic ether component 3 and the alkenyl iodide 4. The tetrahydropyran 3 was stereoselectively synthesized by the 6-endo-cyclization of a hydroxyepoxide prepared from deoxy-D-ribose. The side chain moiety 4 was prepared by the stereoselective hydrostannation of an internal alkyne.",

author = "Isao Kadota and Hiroyoshi Takamura and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan.",

year = "2001",

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doi = "10.1016/S0040-4039(01)00530-5",

language = "English",

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T1 - Synthesis of the J ring segment of gambieric acid

AU - Kadota, Isao

AU - Takamura, Hiroyoshi

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan.

PY - 2001/5/21

Y1 - 2001/5/21

N2 - The J ring segment 2 of gambieric acid was synthesized stereoselectively by the coupling between the cyclic ether component 3 and the alkenyl iodide 4. The tetrahydropyran 3 was stereoselectively synthesized by the 6-endo-cyclization of a hydroxyepoxide prepared from deoxy-D-ribose. The side chain moiety 4 was prepared by the stereoselective hydrostannation of an internal alkyne.

AB - The J ring segment 2 of gambieric acid was synthesized stereoselectively by the coupling between the cyclic ether component 3 and the alkenyl iodide 4. The tetrahydropyran 3 was stereoselectively synthesized by the 6-endo-cyclization of a hydroxyepoxide prepared from deoxy-D-ribose. The side chain moiety 4 was prepared by the stereoselective hydrostannation of an internal alkyne.

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U2 - 10.1016/S0040-4039(01)00530-5

DO - 10.1016/S0040-4039(01)00530-5

M3 - Article

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VL - 42

SP - 3649

EP - 3651

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Synthesis of the J ring segment of gambieric acid

Abstract

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