Total synthesis and absolute configuration of the novel microtubule-stabilizing agent peloruside A

被引：116

作者：

Liao, XB ^{[1
]}

Wu, YS ^{[1
]}

De Brabander, JK ^{[1
]}

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 14期

关键词：

antitumor agents; configuration determination; cyclization; natural products; total synthesis;

D O I：

10.1002/anie.200351145

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unique configuration-dependent mechanistic switch, observed when epimeric seco-acids are subjected to typical Mitsunobu lactonization conditions, is just one of the many unexpected, yet insightful surprises of a synthetic adventure culminating in the first enantioselective total synthesis of the novel microtubule-stabilizing natural product peloruside A (1).

引用

页码：1648 / 1652

页数：5

共 28 条

[1] Mechanistic study of the Mitsunobu reaction [J].

Ahn, CJ ;

Correia, R ;

DeShong, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1751-1753

[2] An approach to the stereoselective synthesis of syn- and anti-1,3-diol derivatives.: Retention of configuration in the Mitsunobu reaction [J].

Ahn, CJ ;

DeShong, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1754-1759

[3] Synthesis of the C1-C21 (C1′-C21′) fragment of the dimeric polyketide natural product SCH 351448 [J].

Bhattacharjee, A ;

Soltani, O ;

De Brabander, JK .

ORGANIC LETTERS, 2002, 4 (04) :481-484

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .13. A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ADDITION OF [(Z)-GAMMA-ALKOXYALLYL]DIISOPINOCAMPHEYLBORANES TO ALDEHYDES [J].

BROWN, HC ;

JADHAV, PK ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1535-1538

[5] MECHANISM OF THE MITSUNOBU ESTERIFICATION REACTION .2. THE INVOLVEMENT OF (ACYLOXY)ALKOXYPHOSPHORANES [J].

CAMP, D ;

JENKINS, ID .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3049-3054

[6] Synthesis of functionalized olefins by cross and ring-closing metatheses [J].

Chatterjee, AK ;

Morgan, JP ;

Scholl, M ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[8]

2-Z

[9]

COREY EJ, 1998, ANGEW CHEM, V110, P2092

[10] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

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