Synthetic study of bicyclo[5.2.1]dec-8-en-4-ones based on tandem anionic [1,3] and oxy-Cope rearrangements of 2-vinylbicyclo[3.2.1]oct-6-en-2-ols

被引：4

作者：

Hashimoto, H

Jin, T

Karikomi, M

Seki, K ^{[1
]}

Haga, K

Uyehara, T

机构：

[1] Utsunomiya Univ, Ctr Instrumental Anal, Utsunomiya, Tochigi 3218585, Japan

[2] Utsunomiya Univ, Fac Engn, Dept Appl Chem, Utsunomiya, Tochigi 3218585, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期

关键词：

taxane skeleton; bicyclic compounds; 1.3] rearrangement; oxy-Cope rearrangement;

D O I：

10.1016/S0040-4039(02)00648-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot synthesis of a 10,10-ethylenebicyclo[5.2.1]dec-8-en-4-one derivative, which can be considered as a synthetic intermediate for the taxane skeleton, has been achieved by tandem anionic [1,3] and oxy-Cope rearrangements of 2-vinylbicyclo[3.2.1] oct-6-en-2-ol. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3633 / 3636

页数：4

共 13 条

[1] A novel method for the synthesis of diquinanes based on anionic [1,3] rearrangement of bicyclo[3.2.1]oct-6-en-2-ols
Hashimoto, H
Abe, Y
Mayuzumi, Y
Karikomi, M
Seki, K
Haga, K
Uyehara, T
TETRAHEDRON LETTERS, 2002, 43 (02) : 265 - 267
[2] Stereoconvergent approach to each of the stereoisomeric hydroxydiquinanes based on the anionic [1,3] rearrangement of bicyclo[3.2.1]oct-6-en-2-ols
Hashimoto, H
Seki, K
Ueno, M
Sato, T
Uyehara, T
TETRAHEDRON LETTERS, 1999, 40 (03) : 511 - 514
[3] Alkoxide-accelerated [1,3] sigmatropic shift of bicyclo[3.2.1]oct-6-en-2-ols to 8-endo-hydroxybicyclo[3.3.0]oct-2-en-4-ones
Chen, YL
Chang, CK
Chang, NC
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1998, 45 (05) : 649 - 653
[4] Oxy-cope rearrangements of bicyclo[3.2.0]heptenones. Synthesis of bicyclo[4.2.1]non-1(4)-en-6-ones and bicyclo[5.2.1]dec-1(10)-en-5-ones
Verma, SK
Nguyen, QH
MacDougall, JM
Fleischer, EB
Moore, HW
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11): : 3379 - 3386
[5] Diquinane synthesis based on anionic [1,3] sigmatropic rearrangements of an oxy-cope system incorporated in the bicyclo[3.2.1]oct-6-ene framework
Seki, K
Kiyokawa, W
Hashimoto, H
Uyehara, T
Ueno, M
Sato, T
CHEMISTRY LETTERS, 1996, (12) : 1035 - 1036
[6] Anionic [1,3] sigmatropic rearrangements of an oxy-cope system incorporated in 8-methylenebicyclo[3.2.1]oct-6-ene and related frameworks
Uyehara, T
Inayama, T
Ueno, M
Sato, T
CHEMISTRY LETTERS, 1996, (05) : 389 - 390
[7] ALKOXIDE-ACCELERATED [1,3] SIGMATROPIC SHIFTS OF BICYCLO[3.2.2]NON-6-EN-2-OLS - SUBSTITUENT EFFECTS AND TANDEM [1,3]-[3,3] SIGMATROPIC REARRANGEMENTS
UYEHARA, T
OHMORI, K
KABASAWA, Y
KATO, T
CHEMISTRY LETTERS, 1984, (11) : 1879 - 1882
[8] REARRANGEMENT APPROACHES TO CYCLIC SKELETONS .3. PRACTICAL ROUTE TO CIS-BICYCLO[4.3.0]NON-4-EN-7-ONES BASED ON PHOTOCHEMICAL [1,3] ACYL MIGRATION OF BICYCLO[3.2.2]NON-6-EN-2-ONES
UYEHARA, T
KABASAWA, Y
FURUTA, T
KATO, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) : 539 - 543
[9] CYCLO-ADDITIONS OF ALLYL CATIONS .21. SYNTHESIS AND H-1-NMR SPECTRA OF BICYCLO[3.2.1]OCTA-2,6-DIENES AND "3-METHYLENEBICYCLO[3.2.1]OCT-6-ENES FROM BICYCLO[3.2.1]OCT-6-EN-3-ONES METHYLATED AT C-2 AND C-4
HOFFMANN, HMR
VATHKE, H
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (11): : 3416 - 3440
[10] (2endo)-2-Chloro-4,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (2) and (2endo)-2-chloro-1,4,4-trimethyl-8-oxabicyclo[3.2.1] oct-6-en-3-one (3) via [4+3]cycloaddition of an oxyallyl intermediate generated from 1,3-dichloro-3-methylbutan-2-one in 2,2,2-trifluoroethanol
Kreiselmeier, Guenter
Menner, Stefan
Foehlisch, Baldur
MOLBANK, 2005, (02)

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