ENANTIOSELECTIVE SYNTHESIS OF (+)-PRESQUALENE DIPHOSPHATE

被引：42

作者：

ROGERS, DH ^{[1
]}

YI, EC ^{[1
]}

POULTER, CD ^{[1
]}

机构：

[1] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 04期

关键词：

D O I：

10.1021/jo00109a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-(1R,2R,3R)-Presqualene diphosphate (PSPP) is an intermediate in the biosynthesis of squalene from farnesyl diphosphate (FPP). The natural 1R,2R,3R enantiomer was synthesized from farnesol in nine steps with greater than or equal to 98% ee. The key step in the synthesis was the stereoselective intramolecular cyclopropanation of farnesyl diazoacetate (5) upon treatment with a chiral rhodium catalyst to give (-)-lactone 6.

引用

页码：941 / 945

页数：5

共 29 条

[1] ENZYMATIC TRANSESTERIFICATIONS OF CARBONATES IN WATER-RESTRICTED ENVIRONMENTS [J].

ABRAMOWICZ, DA ;

KEESE, CR .

BIOTECHNOLOGY AND BIOENGINEERING, 1989, 33 (02) :149-156

[2] SYNTHESIS AND CONVERSION OF PRESQUALENE ALCOHOL TO SQUALENE [J].

ALTMAN, LJ ;

KOWERSKI, RC ;

RILLING, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1782-&

[3] STUDIES IN TERPENE BIOSYNTHESIS - SYNTHESIS AND RESOLUTION OF PRE-SQUALENE AND PRE-PHYTOENE ALCOHOLS [J].

ALTMAN, LJ ;

KOWERSKI, RC ;

LAUNGANI, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6174-6182

[4]

BAXTER A, 1992, J BIOL CHEM, V267, P11705

[5] ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE [J].

BERGSTROM, JD ;

KURTZ, MM ;

REW, DJ ;

AMEND, AM ;

KARKAS, JD ;

BOSTEDOR, RG ;

BANSAL, VS ;

DUFRESNE, C ;

VANMIDDLESWORTH, FL ;

HENSENS, OD ;

LIESCH, JM ;

ZINK, DL ;

WILSON, KE ;

ONISHI, J ;

MILLIGAN, JA ;

BILLS, G ;

KAPLAN, L ;

OMSTEAD, MN ;

JENKINS, RG ;

HUANG, L ;

MEINZ, MS ;

QUINN, L ;

BURG, RW ;

KONG, YL ;

MOCHALES, S ;

MOJENA, M ;

MARTIN, I ;

PELAEZ, F ;

DIEZ, MT ;

ALBERTS, AW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :80-84

[6]

Blankley C. J., 1973, ORG SYNTH, V5, P258

[7] SYNTHESIS OF PRESQUALENE ALCOHOL [J].

CAMPBELL, RV ;

CROMBIE, L ;

PATTENDE.G .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (05) :218-&

[8]

CIOSEK CP, 1993, J BIOL CHEM, V268, P24832

[9] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-PRESQUALENE ALCOHOL [J].

COATES, RM ;

ROBINSON, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1785-&

[10] SYNTHESIS AND C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF ALL-TRANS-GERANYLGERANIOL AND ITS NOR ANALOGS [J].

COATES, RM ;

LEY, DA ;

CAVENDER, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (26) :4915-4922

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