Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel passerini reaction-deprotection-acyl migration strategy

被引：39

作者：

Owens, TD ^{[1
]}

Semple, JE ^{[1
]}

机构：

[1] Corvas Int Inc, Dept Med Chem, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 21期

关键词：

D O I：

10.1021/ol0165239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel variant of the atom-economical Passerini reaction between suitably protected argininal, dipeptide isonitrile, and proline components afforded adduct 13. Orthogonal N-deprotection of 13 led, via a smooth O- to N-acyl migration, to 14, which constitutes the N(10)-C(17) fragment of the cyclotheonamide family of serine protease inhibitors. Each reaction in this three-step protocol proceeds in good yield and under very mild conditions.

引用

页码：3301 / 3304

页数：4

共 48 条

[1] Passerini multicomponent reaction of protected α-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors [J].

Banfi, L ;

Guanti, G ;

Riva, R .

CHEMICAL COMMUNICATIONS, 2000, (11) :985-986

[2] Flexible and convergent total synthesis of cyclotheonamide B [J].

Bastiaans, HMM ;

vanderBaan, JL ;

Ottenheijm, HCJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3880-3889

[3] The identification of α-ketoamides as potent inhibitors of hepatitis C virus NS3-4A proteinase [J].

Bennett, JM ;

Campbell, AD ;

Campbell, AJ ;

Carr, MG ;

Dunsdon, RM ;

Greening, JR ;

Hurst, DN ;

Jennings, NS ;

Jones, PS ;

Jordan, S ;

Kay, PB ;

O'Brien, MA ;

King-Underwood, J ;

Raynham, TM ;

Wilkinson, CS ;

Wilkinson, TCI ;

Wilson, FX .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :355-357

[4] NONORGANOMETALLIC PATHWAY OF THE PASSERINI REACTION ASSISTED BY TITANIUM TETRACHLORIDE [J].

CAROFIGLIO, T ;

COZZI, PG ;

FLORIANI, C ;

CHIESIVILLA, A ;

RIZZOLI, C .

ORGANOMETALLICS, 1993, 12 (07) :2726-2736

[5] Calpain inhibition protects against virus-induced apoptotic myocardial injury [J].

DeBiasi, RL ;

Edelstein, CL ;

Sherry, B ;

Tyler, KL .

JOURNAL OF VIROLOGY, 2001, 75 (01) :351-361

[6]

Deng JG, 1996, TETRAHEDRON LETT, V37, P2261

[7]

Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1

[8] BIOACTIVE MARINE METABOLITES .33. CYCLOTHEONAMIDES, POTENT THROMBIN INHIBITORS, FROM A MARINE SPONGE THEONELLA SP [J].

FUSETANI, N ;

MATSUNAGA, S ;

MATSUMOTO, H ;

TAKEBAYASHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7053-7054

[9]

GIESEMANN G, 1982, J CHEM RES-S, P79

[10] REASSIGNMENT OF STEREOCHEMISTRY AND TOTAL SYNTHESIS OF THE THROMBIN INHIBITOR CYCLOTHEONAMIDE-B [J].

HAGIHARA, M ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6570-6571

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