Stereoselective synthesis of C15-C24 and C25-C30 fragments of dolabelides

被引：29

作者：

Desroy, N

Le Roux, R

Phansavath, P

Chiummiento, L

Bonini, C

Genêt, JP

机构：

[1] Ecole Natl Super Chim Paris, Lab Synthese Select Organ & Prod Nat, UMRCNRS 7573, F-75231 Paris 05, France

[2] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(03)00110-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1763 / 1766

页数：4

相关论文

共 25 条

[1] TOTAL SYNTHESIS OF A FULLY PROTECTED PALYTOXIN CARBOXYLIC-ACID [J].

ARMSTRONG, RW ;

BEAU, JM ;

CHEON, SH ;

CHRIST, WJ ;

FUJIOKA, H ;

HAM, WH ;

HAWKINS, LD ;

JIN, H ;

KANG, SH ;

KISHI, Y ;

MARTINELLI, MJ ;

MCWHORTER, WW ;

MIZUNO, M ;

NAKATA, M ;

STUTZ, AE ;

TALAMAS, FX ;

TANIGUCHI, M ;

TINO, JA ;

UEDA, K ;

UENISHI, J ;

WHITE, JB ;

YONAGA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7525-7530

[2] C-1 REACTIVITY OF 2,3-EPOXY ALCOHOLS VIA OXIRANE OPENING WITH METAL-HALIDES - APPLICATIONS AND SYNTHESIS OF NATURALLY-OCCURRING 2,3-OCTANEDIOL, MURICATACIN, 3-OCTANOL, AND 4-DODECANOLIDE [J].

BONINI, C ;

FEDERICI, C ;

ROSSI, L ;

RIGHI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4803-4812

[3] Preparation of chiral 1,3 skipped anti- and syn-tetrols via highly enantioselective biocatalytic resolution [J].

Bonini, C ;

Chiummiento, L ;

Funicello, M .

TETRAHEDRON-ASYMMETRY, 2001, 12 (19) :2755-2760

[4] A critical outlook and comparison of enantioselective oxidation methodologies of olefins [J].

Bonini, C ;

Righi, G .

TETRAHEDRON, 2002, 58 (25) :4981-5021

[5]

DUGGAN AJ, 1978, TETRAHEDRON LETT, P4323

[6] ABOUT THE STEREOSPECIFIC ALPHA-ALKYLATION OF BETA-HYDROXYESTERS [J].

FRATER, G .

HELVETICA CHIMICA ACTA, 1979, 62 (08) :2825-2828

[7] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[8]

Genet JP, 1996, ACS SYM SER, V641, P31

[9] NOVEL, GENERAL-SYNTHESIS OF THE CHIRAL CATALYSTS DIPHOSPHINE-RUTHENIUM(II) DIALLYL COMPLEXES AND A NEW PRACTICAL IN-SITU PREPARATION OF CHIRAL RUTHENIUM(II) CATALYSTS [J].

GENET, JP ;

PINEL, C ;

RATOVELOMANANAVIDAL, V ;

MALLART, S ;

PFISTER, X ;

DEANDRADE, MCC ;

LAFFITTE, JA .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :665-674

[10] Diastereoselective synthesis of protected syn 1,3-diols:: Preparation of the C16-C24 portion of dolabelides [J].

Grimaud, L ;

de Mesmay, R ;

Prunet, J .

ORGANIC LETTERS, 2002, 4 (03) :419-421