Total synthesis of (±)-hasubanonine

被引：57

作者：

Jones, Spencer B. ^{[1
]}

He, Liwen ^{[1
]}

Castle, Steven L. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 17期

关键词：

D O I：

10.1021/ol0613564

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of the alkaloid (+/-)-hasubanonine is described. A key feature of the route is generation of a phenanthrene intermediate via a Suzuki coupling-Wittig olefination-ring-closing metathesis sequence. Conversion of the phenanthrene into the target molecule required six steps including dearomatization by means of oxidative phenolic coupling, anionic oxy-Cope rearrangement, and a final acid-promoted cyclization. Production of an undesired rearranged product in the last step could be suppressed by moderating the acid strength.

引用

页码：3757 / 3760

页数：4

共 39 条

[1]

BENTLEY KW, 1971, ALKALOIDS, V13, P131

[2]

Cherkaoui MZ, 1997, NEW J CHEM, V21, P1203

[3] ORTHO SUBSTITUTION OF META-ANISALDEHYDE VIA ALPHA-AMINO ALKOXIDE DIRECTED LITHIATION [J].

COMINS, DL ;

BROWN, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3730-3732

[4] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[5] COMPLEMENTARITY OF (4+2) CYCLOADDITION REACTIONS AND [2,3] SIGMATROPIC REARRANGEMENTS IN SYNTHESIS - NEW SYNTHESIS OF FUNCTIONALIZED HASUBANAN DERIVATIVES [J].

EVANS, DA ;

SIMS, CL ;

BRYAN, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (08) :2891-&

[6] TOTAL SYNTHESIS OF NATURALLY OCCURRING SUBSTANCES .2. SYNTHESIS OF HASUBANAN CARBOCYCLIC SYSTEM [J].

EVANS, DA ;

BRYAN, CA ;

WAHL, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (12) :4122-&

[7] [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT [J].

EVANS, DA ;

GOLOB, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4765-4766

[8]

IBUKA T, 1974, CHEM PHARM BULL, V22, P907

[9]

IBUKA T, 1974, CHEM PHARM BULL, V22, P782

[10]

IBUKA T, 1970, TETRAHEDRON LETT, P4811

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