A biosynthetically-inspired synthesis of the tetrahydrofuran core of obtusallenes II and IV

被引：31

作者：

Braddock, D. Christopher ^{[1
]}

Bhuva, Roshni

Millan, David S.

Perez-Fuertes, Yolanda

Roberts, Craig A.

Sheppard, Richard N.

Solanki, Savade

Stokes, Elaine S. E.

White, Andrew J. P.

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

[3] Pfizer Ltd, Global Res & Dev, Sandwich Labs, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 03期

关键词：

D O I：

10.1021/ol062818g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

引用

页码：445 / 448

页数：4

共 22 条

[11]

GUPTA R, 1983, INDIAN J CHEM B, V22, P1011

[12] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[13] QUINONES .7. HALOGENATION AND OXIDATIVE HALOGENATION OF PHENOLS WITH HYDROGEN HALIDES AND HYDROGEN PEROXIDE - SYNTHESIS OF PARA-CHLORANIL AND PARA-BROMANIL [J].

LUBBECKE, H ;

BOLDT, P .

TETRAHEDRON, 1978, 34 (10) :1577-1579

[14]

Murai A., 1999, COMPREHENSIVE NATURA, VI, P303

[15] 2 C-15 BROMOALLENES FROM THE RED ALGA LAURENCIA-OBTUSA [J].

OZTUNC, A ;

IMRE, S ;

LOTTER, H ;

WAGNER, H .

PHYTOCHEMISTRY, 1991, 30 (01) :255-257

[16]

Pohnert G, 2000, EUR J ORG CHEM, V2000, P1821

[17] DRAMATIC CONCENTRATION-DEPENDENCE OF STEREOCHEMISTRY IN THE WITTIG REACTION - EXAMINATION OF THE LITHIUM SALT EFFECT [J].

REITZ, AB ;

NORTEY, SO ;

JORDAN, AD ;

MUTTER, MS ;

MARYANOFF, BE .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3302-3308

[18] A STEREOCHEMICALLY GENERAL-SYNTHESIS OF 2-DEOXYHEXOSES VIA THE ASYMMETRIC ALLYLBORATION OF 2,3-EPOXYALDEHYDES [J].

ROUSH, WR ;

STRAUB, JA ;

VANNIEUWENHZE, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1636-1648

[19] CL-37/CL-35-INDUCED C-13 ISOTOPE SHIFTS IN CHLORINATED METHANES [J].

SERGEYEV, NM ;

SANDOR, P ;

SERGEYEVA, ND ;

RAYNES, WT .

JOURNAL OF MAGNETIC RESONANCE SERIES A, 1995, 115 (02) :174-182

[20] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].

SHARPLESS, KB ;

AMBERG, W ;

BENNANI, YL ;

CRISPINO, GA ;

HARTUNG, J ;

JEONG, KS ;

KWONG, HL ;

MORIKAWA, K ;

WANG, ZM ;

XU, DQ ;

ZHANG, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771

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