A highly efficient synthesis of the hemibrevetoxin B ring system

被引：56

作者：

Rainier, JD ^{[1
]}

Allwein, SP ^{[1
]}

Cox, JM ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991371r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Letter describes the synthesis of the hemibrevetoxin B tetracyclic ring system in 14 linear transformations from the Danishefsky-Kitahara diene.

引用

页码：231 / 234

页数：4

共 28 条

[1] A reiterative synthesis of trans-fused polypyrans via tungsten pentacarbonyl-promoted alkynol endocyclization [J].

Bowman, JL ;

McDonald, FE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3680-3682

[2]

Clark JS, 1997, TETRAHEDRON LETT, V38, P123

[3]

DANISHEFSKY S, 1983, ORG SYNTH, V61, P147

[4] An iterative approach to biologically important fused polycyclic ethers via acyl radical cyclizations [J].

Evans, PA ;

Roseman, JD ;

Garber, LT .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4880-4881

[5] A short, enantioselective synthesis of the AB-ring: Substructure of the brevetoxins via endo-selective alkynol cycloisomerization [J].

Gleason, MM ;

McDonald, FE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6432-6435

[6] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

[7] Stereocontrolled total synthesis of hemibrevetoxin B [J].

Kadota, I ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6597-6606

[8] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRONES VIA FORMAL HETERO-DIELS-ALDER REACTIONS OF DANISHEFSKYS DIENE WITH ALDEHYDES [J].

KECK, GE ;

LI, XY ;

KRISHNAMURTHY, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :5998-5999

[9] ISOLATION AND STRUCTURE OF BREVETOXIN-B FROM THE RED TIDE DINOFLAGELLATE PTYCHODISCUS-BREVIS (GYMNODINIUM, BREVE) [J].

LIN, YY ;

RISK, M ;

RAY, SM ;

VANENGEN, D ;

CLARDY, J ;

GOLIK, J ;

JAMES, JC ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6773-6775

[10] Synthesis of trans-syn-trans fused bis-pyrans via endo-selective cyclizations of cyclic sulfates [J].

McDonald, FE ;

Vadapally, P .

TETRAHEDRON LETTERS, 1999, 40 (12) :2235-2238

← 1 2 3 →