Synthesis of the C22-C26 tetrahydropyran segment of phorboxazole by a stereoselective Prins cyclization

被引：143

作者：

Rychnovsky, SD ^{[1
]}

Thomas, CR ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005646a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrahydropyran rings are found in many complex natural products, and the segment-coupling Prins cyclization is an effective strategy for their synthesis. We report a four-step, stereoselective synthesis of the C20-C27 tetrahydropyran segment of phorboxazole. The key step is a Prins cyclization induced by catalytic BF3. OEt2.

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页码：1217 / 1219

页数：3

相关论文

共 42 条

[1]

ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661

[2] Convergent synthesis of the C31-C46 domain of the phorboxazole natural products [J].

Ahmed, F ;

Forsyth, CJ .

TETRAHEDRON LETTERS, 1998, 39 (3-4) :183-186

[3] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .30. E-PENTENYLBORONATES AND Z-PENTENYLBORONATES, REAGENTS FOR SIMPLE DIASTEREOSELECTION ON ADDITION TO ALDEHYDES [J].

ANDERSEN, MW ;

HILDEBRANDT, B ;

KOSTER, G ;

HOFFMANN, RW .

CHEMISCHE BERICHTE, 1989, 122 (09) :1777-1782

[4] THE SYNTHESIS OF 4-HALOTETRAHYDROPYRANS AND 4-HALO-5,6-DIHYDRO-2H-PYRANS VIA THE LEWIS ACID PROMOTED CYCLIZATION OF ACETALS OF HOMOALLYLIC AND HOMOPROPARGYLIC ALCOHOLS [J].

BUNNELLE, WH ;

SEAMON, DW ;

MOHLER, DL ;

BALL, TF ;

THOMPSON, DW .

TETRAHEDRON LETTERS, 1984, 25 (25) :2653-2654

[5] Stereoselective synthesis of the C3-C17 bis-oxane domain of phorboxazole A [J].

Cink, RD ;

Forsyth, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5672-5673

[6] Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].

Cloninger, MJ ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093

[7] LEWIS ACID MEDIATED CONDENSATION OF ALKENOLS AND ALDEHYDES - A SELECTIVE SYNTHESIS OF TETRAHYDROPYRANS AND OXEPANES [J].

COPPI, L ;

RICCI, A ;

TADDEI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :911-913

[8] General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].

Dahanukar, VH ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320

[9] Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus [J].

Evans, DA ;

Cee, VJ ;

Smith, TE ;

Santiago, KJ .

ORGANIC LETTERS, 1999, 1 (01) :87-90

[10] Total synthesis of phorboxazole A [J].

Forsyth, CJ ;

Ahmed, F ;

Cink, RD ;

Lee, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5597-5598

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