SYNTHESIS OF ABC TAXOID RING-SYSTEMS VIA A CONVERGENT STRATEGY

被引：46

作者：

NICOLAOU, KC ^{[1
]}

YANG, Z ^{[1
]}

SORENSEN, EJ ^{[1
]}

NAKADA, M ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO, DEPT CHEM, LA JOLLA, CA 92093 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 12期

关键词：

D O I：

10.1039/c39930001024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Intermediates 4 and 5 have been coupled via a Shapiro reaction to afford compound 6 which has been further elaborated to the ABC taxoid systems 11 and 12 via a McMurry pinacol cyclization to 11 followed by oxidation to 12.

引用

页码：1024 / 1026

页数：3

共 14 条

[1] TOTAL SYNTHESIS OF VERTICILLENE - A BIOMIMETIC APPROACH TO THE TAXANE FAMILY OF ALKALOIDS [J].

BEGLEY, MJ ;

JACKSON, CB ;

PATTENDEN, G .

TETRAHEDRON, 1990, 46 (13-14) :4907-4924

[2]

CUSACK NJ, 1976, TETRAHEDRON, V32, P2157, DOI 10.1016/0040-4020(76)85128-9

[3]

Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13

[4] TOTAL SYNTHESIS OF VERTICILLENE, THE PUTATIVE BIOGENETIC PRECURSOR OF THE TAXANE ALKALOIDS [J].

JACKSON, CB ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1985, 26 (28) :3393-3396

[5] SYNTHESIS OF A TAXANE TRIENE [J].

KENDE, AS ;

JOHNSON, S ;

SANFILIPPO, P ;

HODGES, JC ;

JUNGHEIM, LN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3513-3515

[6] A CONVERGENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALKENES [J].

MARTIN, SF ;

DANIEL, D ;

CHERNEY, RJ ;

LIRAS, S .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2523-2525

[7] CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].

MCMURRY, JE .

CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524

[8] SYNTHESIS OF 1,2-CYCLOALKANEDIOLS BY INTRAMOLECULAR TITANIUM-INDUCED PINACOL COUPLING [J].

MCMURRY, JE ;

RICO, JG .

TETRAHEDRON LETTERS, 1989, 30 (10) :1169-1172

[9] AN OPTIMIZED PROCEDURE FOR TITANIUM-INDUCED CARBONYL COUPLING [J].

MCMURRY, JE ;

LECTKA, T ;

RICO, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3748-3749

[10] REDUCTION OF CIS-BICYCLO[4.3.0]NON-3-ENE AND ITS 8-SUBSTITUTED HETEROCYCLIC-ANALOGS [J].

MUNDY, BP ;

THEODORE, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2005-2010

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