Enantioselective total synthesis of batzelladine A

被引：60

作者：

Shimokawa, J ^{[1
]}

Shirai, K ^{[1
]}

Tanatani, A ^{[1
]}

Hashimoto, Y ^{[1
]}

Nagasawa, K ^{[1
]}

机构：

[1] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 12期

关键词：

alkaloids; cycloaddition; natural products; oxidation; total synthesis;

D O I：

10.1002/anie.200353200

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One-step formation of an enone from a primary alcohol has been effectively applied in the total synthesis of batzelladine A (1). Successive 1,3-dipolar cycloadditions with a subsequent cyclization were used to form the tricyclic guanidine subunit of this natural product, which has the strongest inhibitory activity of HIV gp120-CD4 binding among the batzelladines.

引用

页码：1559 / 1562

页数：4

共 35 条

[21] Tuning stereoselection in tethered Biginelli condensations.: Synthesis of cis- or trans-1-oxo- and 1-iminohexahydropyrrolo[1,2-c]pyrimidine [J].

McDonald, AI ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1520-1528

[22] NEW SYNTHETIC METHODS FOR ALPHA, BETA-UNSATURATED KETONES, ALDEHYDES, ESTERS AND LACTONES BY THE PALLADIUM-CATALYZED REACTIONS OF SILYL ENOL ETHERS, KETENE SILYL ACETALS, AND ENOL ACETATES WITH ALLYL CARBONATES [J].

MINAMI, I ;

TAKAHASHI, K ;

SHIMIZU, I ;

KIMURA, T ;

TSUJI, J .

TETRAHEDRON, 1986, 42 (11) :2971-2977

[23] Stereoselective synthesis of tricyclic guanidine, the key component of the batzelladine alkaloids [J].

Nagasawa, K ;

Ishiwata, T ;

Hashimoto, Y ;

Nakata, T .

TETRAHEDRON LETTERS, 2002, 43 (36) :6383-6385

[24] Stereoselective synthesis of tricyclic guanidine systems: confirmation of the stereochemistry of batzelladine F left-hand tricyclic guanidine portion [J].

Nagasawa, K ;

Koshino, H ;

Nakata, T .

TETRAHEDRON LETTERS, 2001, 42 (25) :4155-4158

[25] A new method for the one-step synthesis of α,β-unsaturated carbonyl systems from saturated alcohols and carbonyl compounds [J].

Nicolaou, KC ;

Zhong, YL ;

Baran, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (31) :7596-7597

[26] NOVEL ALKALOIDS FROM THE SPONGE BATZELLA SP - INHIBITORS OF HIV GP120-HUMAN CD4 BINDING [J].

PATIL, AD ;

KUMAR, NV ;

KOKKE, WC ;

BEAN, MF ;

FREYER, AJ ;

DEBROSSE, C ;

MAI, S ;

TRUNEH, A ;

FAULKNER, DJ ;

CARTE, B ;

BREEN, AL ;

HERTZBERG, RP ;

JOHNSON, RK ;

WESTLEY, JW ;

POTTS, BCM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1182-1188

[27] Batzelladines F-I, novel alkaloids from the sponge Batzella sp.: Inducers of p56(lck)-CD4 dissociation [J].

Patil, AD ;

Freyer, AJ ;

Taylor, PB ;

Carte, B ;

Zuber, G ;

Johnson, RK ;

Faulkner, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1814-1819

[28] AN ENANTIOSPECIFIC SYNTHESIS OF THE TRICYCLIC GUANIDINE SEGMENT OF THE ANTI-HIV MARINE ALKALOID BATZELLADINE-A [J].

RAO, AVR ;

GURJAR, MK ;

VASUDEVAN, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1369-1370

[29] ELECTROPHILIC AND NUCLEOPHILIC ORGANOSELENIUM REAGENTS - NEW ROUTES TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

SHARPLES.KB ;

LAUER, RF ;

TERANISH.AY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6137-6139

[30] Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D [J].

Snider, BB ;

Chen, JS ;

Patil, AD ;

Freyer, AJ .

TETRAHEDRON LETTERS, 1996, 37 (39) :6977-6980

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