Total synthesis of (±)-spiroxin C

被引：42

作者：

Miyashita, K ^{[1
]}

Sakai, T ^{[1
]}

Imanishi, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 15期

关键词：

D O I：

10.1021/ol034856v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of a marine-derived potent antitumor antibiotic, (+/-)-spiroxin C, was achieved via a TBAF-activated Suzuki-Miyaura cross-coupling reaction as a key step, which was also shown to be useful for the synthesis of sterically hindered binaphthyl derivatives.

引用

页码：2683 / 2686

页数：4

共 28 条

[1] HOST GUEST COMPLEXATION .33. SEARCH FOR NEW CHIRAL HOSTS [J].

ARTZ, SP ;

DEGRANDPRE, MP ;

CRAM, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1486-1496

[2] Unified route to the palmarumycin and preussomerin natural products. Enantioselective synthesis of (-)-preussomerin G [J].

Barrett, AGM ;

Blaney, F ;

Campbell, AD ;

Hamprecht, D ;

Meyer, T ;

White, AJP ;

Witty, D ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :2735-2750

[3] Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371:: novel spiro-ketal fungal metabolites [J].

Barrett, AGM ;

Hamprecht, D ;

Meyer, T .

CHEMICAL COMMUNICATIONS, 1998, (07) :809-810

[4] Total syntheses of (±)-preussomerins G and I [J].

Chi, S ;

Heathcock, CH .

ORGANIC LETTERS, 1999, 1 (01) :3-5

[5] PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES [J].

COMINS, DL ;

DEHGHANI, A .

TETRAHEDRON LETTERS, 1992, 33 (42) :6299-6302

[6] Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide [J].

Corminboeuf, O ;

Renaud, P .

ORGANIC LETTERS, 2002, 4 (10) :1731-1733

[7] Sequential transformations of 1,3-dibora butadienes to enones or tetrasubstituted 1,3-butadienes [J].

Desurmont, G ;

Dalton, S ;

Giolando, DM ;

Srebnik, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7943-7946

[8] ENANTIOSELECTIVE PROTONATION OF ENOLATES - NOVEL CHIRAL PROTON SOURCES AND REMARKABLE EFFECTS OF THE COUNTERCATION [J].

FUJI, K ;

KAWABATA, T ;

KURODA, A ;

TAGA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :1914-1915

[9]

Fuji K, 1997, CHEM PHARM BULL, V45, P1524

[10] Palladium-catalyzed asymmetric reduction of allylic esters with a new chiral monodentate ligand, 8-diphenylphosphino-8′-methoxy-1,1′-binaphthyl [J].

Fuji, K ;

Sakurai, M ;

Kinoshita, T ;

Kawabata, T .

TETRAHEDRON LETTERS, 1998, 39 (35) :6323-6326

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