Short synthesis of the 6,6-spiroketal cores of spirofungins A and B

被引：37

作者：

Dias, LC ^{[1
]}

de Oliveira, LG ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 15期

关键词：

D O I：

10.1021/ol0491078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach uses a very efficient alkylation of a lithiated N,N-dimethylhydrazone followed by spiroketal formation under acidic conditions.

引用

页码：2587 / 2590

页数：4

共 19 条

[1]

BLOCH R, 1991, SYNLETT, P829

[2] Conjugate reduction of α,β-unsaturated carbonyl compounds.: Selective inhibition of benzyl ether hydrogenolysis by NH4OH/MeOH [J].

Dias, LC ;

Campano, PL .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1998, 9 (01) :97-99

[3] TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC CP-61,405 (ROUTIENNOCIN) [J].

DIEZMARTIN, D ;

KOTECHA, NR ;

LEY, SV ;

MANTEGANI, S ;

MENENDEZ, JC ;

ORGAN, HM ;

WHITE, AD ;

BANKS, BJ .

TETRAHEDRON, 1992, 48 (37) :7899-7938

[4] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].

EVANS, DA ;

BENDER, SL ;

MORRIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526

[5] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[6]

EVANS DA, 2001, J ORG CHEM, V66, P7001

[7]

GAGE JR, 1990, ORG SYNTH, V68, P83

[8] 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

[9]

Höltzel A, 1998, J ANTIBIOT, V51, P699

[10] AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES [J].

LEVIN, JI ;

TUROS, E ;

WEINREB, SM .

SYNTHETIC COMMUNICATIONS, 1982, 12 (13) :989-993

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