Toward the total synthesis of variecolin

被引：65

作者：

Molander, GA ^{[1
]}

Quirmbach, MS ^{[1
]}

Silva, LF ^{[1
]}

Spencer, KC ^{[1
]}

Balsells, J ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 15期

关键词：

D O I：

10.1021/ol015763l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An annulative approach toward the total synthesis of the sesterterpenoid variecolin (1) is presented. Synthesis of the key hemiketal, containing the core ABC ring skeleton, has been achieved on a model system by an expeditious route utilizing samarium(ll) iodide. Furthermore, enantioselective syntheses of component fragments for the total synthesis have been developed.

引用

页码：2257 / 2260

页数：4

共 22 条

[1] TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].

APPEL, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3] SYNTHESIS OF BICYCLO[4.2.0]OCTANE-7,8-DIOL, A DERIVATIVE OF CYCLOOCTATETRAENE DICHLORIDE [J].

COPE, AC ;

HERRICK, EC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :983-987

[4]

Fujimoto H, 2000, CHEM PHARM BULL, V48, P1436, DOI 10.1248/cpb.48.1436

[5] ENZYME-CATALYZED ASYMMETRIC-SYNTHESIS .8. ENANTIOSELECTIVITY OF PIG-LIVER ESTERASE CATALYZED HYDROLYSES OF 4-SUBSTITUTED MESO CYCLOPENTANE 1,2-DIESTERS [J].

GAIS, HJ ;

BULOW, G ;

ZATORSKI, A ;

JENTSCH, M ;

MAIDONIS, P ;

HEMMERLE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5115-5122

[6]

GAIS HJ, 1992, SYNTHESIS-STUTTGART, P169

[7]

Hajos Z. G., 1985, ORG SYNTH, V63, P26

[8] ASYMMETRIC HYDROLYSIS AND ESTERIFICATION CATALYZED BY ESTERASES FROM PORCINE PANCREAS IN THE SYNTHESIS OF BOTH ENANTIOMERS OF CYCLOPENTANOID BUILDING-BLOCKS [J].

HEMMERLE, H ;

GAIS, HJ .

TETRAHEDRON LETTERS, 1987, 28 (30) :3471-3474

[9]

HEMMERLE H, 1990, THESIS U FREIBURG

[10] VARIECOLIN, A SESTERTERPENOID OF NOVEL SKELETON FROM ASPERGILLUS-VARIECOLOR MF138 [J].

HENSENS, OD ;

ZINK, D ;

WILLIAMSON, JM ;

LOTTI, VJ ;

CHANG, RSL ;

GOETZ, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3399-3403

← 1 2 3 →