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

[31]

SHIOTANI S, 1976, TETRAHEDRON LETT, P767

[32] THE ALKALOIDS OF STEPHANIA-ELEGANS [J].

SINGH, RS ;

KUMAR, P ;

BHAKUNI, DS .

JOURNAL OF NATURAL PRODUCTS, 1981, 44 (06) :664-667

[33] DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS [J].

SNIECKUS, V .

CHEMICAL REVIEWS, 1990, 90 (06) :879-933

[34]

TOMITA M, 1965, CHEM PHARM BULL, V13, P538

[35]

TOMITA M, 1964, TETRAHEDRON LETT, P2937

[36]

Trauner D, 1998, SYNTHESIS-STUTTGART, P653

[37] A novel approach to erythrinan alkaloids by utilizing substituted biphenyl as building block [J].

Yasui, Y ;

Koga, Y ;

Suzuki, K ;

Matsumoto, T .

SYNLETT, 2004, (04) :615-618

[38] Highly functionalized bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C60 [J].

Yen, CF ;

Peddinti, RK ;

Liao, CC .

ORGANIC LETTERS, 2000, 2 (18) :2909-2912

[39] An improved preparation of arylboronates: Application in one-pot Suzuki biaryl synthesis [J].

Zhu, L ;

Duquette, J ;

Zhang, MB .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3729-3732

← 1 2 3 4 →