Efficient synthesis of (±)-γ-lycorane employing stereoselective conjugate addition to nitroolefin

被引：29

作者：

Yasuhara, T

Osafune, E

Nishimura, K

Yamashita, M

Yamada, K

Muraoka, O

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Kinki Univ, Sch Pharmaceut Sci, Higashiosaka, Osaka 5778502, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 15期

基金：

日本学术振兴会;

关键词：

alkaloid; synthesis; nitroolefin; addition;

D O I：

10.1016/j.tetlet.2004.02.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-gamma-Lycorane 3 was synthesized in 52% overall yield via seven steps from 5 by employing the highly stereoselective nitro-Michael cyclization of 5 to 9 and diastereoselective conjugate addition of aryllithium to a nitroolefin 10 as two key steps. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3043 / 3045

页数：3

相关论文

共 61 条

[1] A STEREOSELECTIVE FORMAL SYNTHESIS OF (+/-)-(GAMMA)-LYCORANE [J].

ANGLE, SR ;

BOYCE, JP .

TETRAHEDRON LETTERS, 1995, 36 (35) :6185-6188

[2]

BAECKVALL JE, 1991, J ORG CHEM, V56, P2988

[3] A NEW, HIGHLY EFFICIENT SYNTHESIS OF CONJUGATED NITROCYCLOALKENES [J].

BALLINI, R ;

PALESTINI, C .

TETRAHEDRON LETTERS, 1994, 35 (31) :5731-5734

[4] Electrocyclic ring-opening/π-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates:: Application to syntheses of (±)-, (+)-, and (-)-γ-lycorane [J].

Banwell, MG ;

Harvey, JE ;

Hockless, DCR ;

Wu, AW .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4241-4250

[5] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-GAMMA-LYCORANE [J].

BANWELL, MG ;

WU, AW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2671-2672

[6]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[7]

Cassayre J, 1999, SYNLETT, P501

[8] KINETICALLY AND THERMODYNAMICALLY CONTROLLED SYNTHESIS OF 2,6-DISUBSTITUTED CYCLOHEXANONE SEMICARBAZONES - A MOLECULAR MECHANICS STUDY OF A1,3-STRAIN [J].

CASTELLO, A ;

JAIME, C ;

MARQUET, J ;

MORENOMANAS, M .

TETRAHEDRON, 1985, 41 (18) :3791-3802

[9] Enantioselective Michael addition of nitromethane to α,β-enones catalyzed by chiral quaternary ammonium salts.: A simple synthesis of (R)-baclofen [J].

Corey, EJ ;

Zhang, FY .

ORGANIC LETTERS, 2000, 2 (26) :4257-4259

[10]

Cossy J, 1999, EUR J ORG CHEM, V1999, P1925

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