Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3

Mitsunori Kanemoto, Michio Murata, Tohru Oishi

研究成果: ジャーナルへの寄稿記事

22 引用 (Scopus)

抄録

(Chemical Equation Presented) A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an intermediate that was then cross-coupled to afford an E,E-diene system. Four contiguous stereogenic centers were installed via construction of the tetrahydropyran ring by means of Katsuki-Sharpless asymmetric epoxidation, 6-endo-tet cyclization, and Sharpless asymmetric dihydroxylation.

元の言語英語
ページ(範囲)8810-8813
ページ数4
ジャーナルJournal of Organic Chemistry
74
発行部数22
DOI
出版物ステータス出版済み - 11 20 2009
外部発表Yes

Fingerprint

Alkenes
Epoxidation
Cyclization
amphidinol 3

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

これを引用

Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3. / Kanemoto, Mitsunori; Murata, Michio; Oishi, Tohru.

:: Journal of Organic Chemistry, 巻 74, 番号 22, 20.11.2009, p. 8810-8813.

研究成果: ジャーナルへの寄稿記事

Kanemoto, Mitsunori ; Murata, Michio ; Oishi, Tohru. / Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3. :: Journal of Organic Chemistry. 2009 ; 巻 74, 番号 22. pp. 8810-8813.
@article{378a5561ba5c4578bb1f203776bea632,
title = "Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3",
abstract = "(Chemical Equation Presented) A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an intermediate that was then cross-coupled to afford an E,E-diene system. Four contiguous stereogenic centers were installed via construction of the tetrahydropyran ring by means of Katsuki-Sharpless asymmetric epoxidation, 6-endo-tet cyclization, and Sharpless asymmetric dihydroxylation.",
author = "Mitsunori Kanemoto and Michio Murata and Tohru Oishi",
year = "2009",
month = "11",
day = "20",
doi = "10.1021/jo901793f",
language = "English",
volume = "74",
pages = "8810--8813",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

T1 - Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3

AU - Kanemoto, Mitsunori

AU - Murata, Michio

AU - Oishi, Tohru

PY - 2009/11/20

Y1 - 2009/11/20

N2 - (Chemical Equation Presented) A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an intermediate that was then cross-coupled to afford an E,E-diene system. Four contiguous stereogenic centers were installed via construction of the tetrahydropyran ring by means of Katsuki-Sharpless asymmetric epoxidation, 6-endo-tet cyclization, and Sharpless asymmetric dihydroxylation.

AB - (Chemical Equation Presented) A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an intermediate that was then cross-coupled to afford an E,E-diene system. Four contiguous stereogenic centers were installed via construction of the tetrahydropyran ring by means of Katsuki-Sharpless asymmetric epoxidation, 6-endo-tet cyclization, and Sharpless asymmetric dihydroxylation.

UR - http://www.scopus.com/inward/record.url?scp=70449640055&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70449640055&partnerID=8YFLogxK

U2 - 10.1021/jo901793f

DO - 10.1021/jo901793f

M3 - Article

C2 - 19852459

AN - SCOPUS:70449640055

VL - 74

SP - 8810

EP - 8813

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 22

ER -