Consecutive sigmatropic rearrangements in the enantioselective total synthesis of (-)-joubertinamine and (-)-mesembrine

被引：36

作者：

Ilardi, Elizabeth A. ^{[1
]}

Isaacman, Michael J. ^{[1
]}

Qin, Ying-chuan ^{[1
]}

Shelly, Sommer A. ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 16期

基金：

美国国家科学基金会;

关键词：

Sigmatropic rearrangements; Sceletium alkaloids; Mesembrine; Joubertinamine; QUATERNARY CARBON CENTER; ASYMMETRIC-SYNTHESIS; CLAISEN REARRANGEMENT; PINNATOXINS; (+/-)-MESEMBRINE; JOUBERTINAMINE; (+)-MESEMBRINE; CYCLOADDITION; SUBSTITUTION; ALKALOIDS;

D O I：

10.1016/j.tet.2008.10.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Joubertinamine and mesembrine are two related alkaloids isolated from Sceletium plants. From the perspective of chemical synthesis, the major challenge posed by joubertinamine and mesembrine is Undoubtedly the construction of the benzylic quaternary stereogenic center. We became intrigued by the prospect of applying Successive sigmatropic rearrangements to build the key structural features of these alkaloids in enantioselective manner. In this article, We detail Our results in this area, which include the enantioselective total synthesis Of (-)-joubertinamine and (-)-mesembrine. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3261 / 3269

页数：9

共 39 条

[1] Synthesis and applications of C2-symmetric guanidine bases [J].

Allingham, MT ;

Howard-Jones, A ;

Murphy, PJ ;

Thomas, DA ;

Caulkett, PWR .

TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680

[2]

BUCHI G, 1970, J AM CHEM SOC, V92, P3126

[3] A simple and efficient synthesis of (±)-mesembrine [J].

Chavan, SP ;

Khobragade, DA ;

Pathak, AB ;

Kalkote, UR .

TETRAHEDRON LETTERS, 2004, 45 (27) :5263-5265

[4] A concise synthesis of (-)-mesembrine [J].

Dalko, PI ;

Brun, V ;

Langlois, Y .

TETRAHEDRON LETTERS, 1998, 39 (49) :8979-8982

[5] Asymmetric construction of a quaternary carbon center by tandem [4+2]/[3+2] cycloaddition of a nitroalkene. The total synthesis of (-)-mesembrine [J].

Denmark, SE ;

Marcin, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1675-1686

[6] ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS [J].

EVANS, DA ;

ANDREWS, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (05) :147-155

[7] NUCLEOPHILIC CLEAVAGE OF ALLYLIC SULFENATE ESTERS - MECHANISTIC OBSERVATIONS [J].

EVANS, DA ;

ANDREWS, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (10) :3672-&

[8] The Claisen rearrangement. Response to solvents and substituents: The case for both hydrophobic and hydrogen bond acceleration in water and for a variable transition state [J].

Gajewski, JJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (05) :219-225

[9] CEPHALOTAXINE ANALOGS - STEREOSPECIFIC SYNTHESIS OF SPIRO-FUSED 3-BENZAZEPINE AND 1,3-BENZODIAZEPINE DERIVATIVES [J].

GARDINER, JM ;

BRYCE, MR ;

BATES, PA ;

HURSTHOUSE, MB .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1261-1266

[10] An olefination approach to the enantioselective syntheses of several styryllactones [J].

Harris, JM ;

O'Doherty, GA .

TETRAHEDRON, 2001, 57 (24) :5161-5171

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