Total Synthesis of (-)-Leuconicine A and B

被引：59

作者：

Sirasani, Gopal ^{[1
]}

Andrade, Rodrigo B. ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 17期

关键词：

STRYCHNOS ALKALOIDS;

D O I：

10.1021/ol202056w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise asymmetric total syntheses of Strychnos alkaloids (-)-leuconicine A (14 steps, 9% overall yield) and B (13 steps, 10% overall yield) have been accomplished. Key steps include (1) our sequential one-pot spiro-cyclization/intramolecular aza-Baylis-Hillman method to prepare the ABCE framework; (2) a novel domino acylation/Knoevenagel cyclization to prepare the F-ring; and (3) a Heck cyclization to access the D-ring.

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收藏

页码：4736 / 4737

页数：2

相关论文

共 13 条

[1]

[Anonymous], 1977, Tetrahedron Letters

[2] Leuconicines A-G and (-)-Eburnamaline, Biologically Active Strychnan and Eburnan Alkaloids from Leuconotis [J].

Gan, Chew-Yan ;

Low, Yun-Yee ;

Etoh, Tadahiro ;

Hayashi, Masahiko ;

Komiyama, Kanki ;

Kam, Toh-Seok .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (12) :2098-2103

[3] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[4] Stereoselective α-Aminoallylation of Aldehydes with Chiral tert-Butanesulfinamides and Allyl Bromides [J].

Gonzalez-Gomez, Jose C. ;

Medjahdi, Mohamed ;

Foubelo, Francisco ;

Yus, Miguel .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) :6308-6311

[5] NOTES ON THE ALKALOIDS OF PICRALIMA [J].

MILLSON, MF ;

ROBINSON, R ;

THOMAS, AF .

EXPERIENTIA, 1953, 9 (03) :89-91

[6] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].

NAHM, S ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818

[7] A CONVENIENT METHOD FOR THE SELECTIVE REDUCTION OF AMIDES TO AMINES [J].

RAUCHER, S ;

KLEIN, P .

TETRAHEDRON LETTERS, 1980, 21 (42) :4061-4064

[8] A GENERAL-SOLUTION TO THE SYNTHESIS OF 2-AZABICYCLO[3.3.1]NONANE UNIT OF STRYCHNOS ALKALOIDS [J].

RAWAL, VH ;

MICHOUD, C .

TETRAHEDRON LETTERS, 1991, 32 (14) :1695-1698

[9] GENERAL STRATEGY FOR THE STEREOCONTROLLED SYNTHESIS OF STRYCHNOS ALKALOIDS - A CONCISE SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].

RAWAL, VH ;

MICHOUD, C ;

MONESTEL, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :3030-3031

[10] Synthesis and Applications of tert-Butanesulfinamide [J].

Robak, MaryAnn T. ;

Herbage, Melissa A. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (06) :3600-3740