Lasonolide A: Structural revision and synthesis of the unnatural (-)-enantiomer

被引：76

作者：

Lee, E ^{[1
]}

Song, HY ^{[1
]}

Kang, JW ^{[1
]}

Kim, DS ^{[1
]}

Jung, CK ^{[1
]}

Joo, JM ^{[1
]}

机构：

[1] Seoul Natl Univ, Sch Chem & Mol Engn, Seoul 151747, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 03期

关键词：

D O I：

10.1021/ja017265d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of the unnatural (-)-enantiomer of lasonolide A was achieved starting from ethyl l-malate. The two tetrahydropyranyl fragments were prepared stereoselectively via radical cyclization reactions of β-alkoxyacrylates. The full structure of natural lasonolide A was determined unequivocally. Copyright © 2002 American Chemical Society.

引用

页码：384 / 385

页数：2

共 17 条

[1]

Beck H, 1999, EUR J ORG CHEM, V1999, P2991

[2]

Blakemore PR, 1998, SYNLETT, P26

[3] A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].

CHEN, KM ;

GUNDERSON, KG ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

CHEMISTRY LETTERS, 1987, (10) :1923-1926

[4] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].

EVANS, DA ;

KALDOR, SW ;

JONES, TK ;

CLARDY, J ;

STOUT, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031

[5] Stereocontrolled synthesis of spirocyclopropane sugars and their application to asymmetric formation of tertiary chiral centres: A route to 2,2'-dialkylated pyranose subunit (C-18-C-23) of lasonolide A [J].

Gurjar, MK ;

Kumar, P ;

Rao, BV .

TETRAHEDRON LETTERS, 1996, 37 (47) :8617-8620

[6] Preparation of 4,5-cyclopropylsugar derivatives: Application to the stereocontrolled synthesis of bottom half (C-7-C-16) segment of lasonolide A [J].

Gurjar, MK ;

Chakrabarti, A ;

Rao, BV ;

Kumar, P .

TETRAHEDRON LETTERS, 1997, 38 (39) :6885-6888

[7] LASONOLIDE-A, A NEW CYTOTOXIC MACROLIDE FROM THE MARINE SPONGE FORCEPIA SP [J].

HORTON, PA ;

KOEHN, FE ;

LONGLEY, RE ;

MCCONNELL, OJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6015-6016

[8] CHIRALITY TRANSMISSION VIA A 6-ENDO FREE-RADICAL-MEDIATED CYCLIZATION PROCESS - REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF THE 22-HYDROXYLATED STEROID SIDE-CHAINS [J].

KOREEDA, M ;

GEORGE, IA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8098-8100

[9] Total synthesis of pamamycin-607 [J].

Lee, E ;

Jeong, EJ ;

Kang, EJ ;

Sung, LT ;

Hong, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) :10131-10132

[10] TOTAL SYNTHESIS OF DACTOMELYNES [J].

LEE, E ;

PARK, CM ;

YUN, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (30) :8017-8018

← 1 2 →