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.

引用

收藏

页码：1217 / 1219

页数：3

相关论文

共 42 条

[21] STEREOSELECTIVE APPROACH TO TRISUBSTITUTED TETRAHYDROFURANS [J].

MOHR, P .

TETRAHEDRON LETTERS, 1993, 34 (39) :6251-6254

[22] Absolute configuration of phorboxazoles A and B from the marine sponge, Phorbas sp .2. C43 and complete stereochemistry [J].

Molinski, TF .

TETRAHEDRON LETTERS, 1996, 37 (44) :7879-7880

[23] PREPARATION OF CYCLIC ETHERS VIA A TRANSACETALIZATION-CATIONIC CYCLIZATION SEQUENCE [J].

NIKOLIC, NA ;

GONDA, E ;

LONGFORD, CPD ;

LANE, NT ;

THOMPSON, DW .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2748-2751

[24] TOTAL SYNTHESIS OF (-)-LAURENYNE - USE OF ACETAL-INITIATED CYCLIZATIONS TO PREPARE FUNCTIONALIZED 8-MEMBERED CYCLIC ETHERS [J].

OVERMAN, LE ;

THOMPSON, AS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2248-2256

[25] Towards the total synthesis of phorboxazoles A and B:: Stereocontrolled synthesis of a C20-C32 subunit [J].

Paterson, I ;

Arnott, EA .

TETRAHEDRON LETTERS, 1998, 39 (39) :7185-7188

[26] Synthetic studies towards phorboxazole A. A convergent synthesis of the C31-C46 polyene oxane-hemiacetal side chain [J].

Pattenden, G ;

Plowright, AT ;

Tornos, JA ;

Ye, T .

TETRAHEDRON LETTERS, 1998, 39 (33) :6099-6102

[27] Prins desymmetrization of a C-2-symmetric diol: Application to the synthesis of 17-deoxyroflamycoin [J].

Rychnovsky, SD ;

Yang, G ;

Hu, YQ ;

Khire, UR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3022-3023

[28] Segment-coupling prins cyclizations [J].

Rychnovsky, SD ;

Hu, YQ ;

Ellsworth, B .

TETRAHEDRON LETTERS, 1998, 39 (40) :7271-7274

[29] Palladium-catalyzed cross-coupling of terminal alkynes with 4-trifloyloxazole: Studies toward the construction of the C26-C31 subunit of phorboxazole A [J].

Schaus, JV ;

Panek, JS .

ORGANIC LETTERS, 2000, 2 (04) :469-471

[30] PHORBOXAZOLE-A AND PHORBOXAZOLE-B - POTENT CYTOSTATIC MACROLIDES FROM MARINE SPONGE PHORBAS SP [J].

SEARLE, PA ;

MOLINSKI, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8126-8131

← 1 2 3 4 5 →