Studies in marine macrolide synthesis: Synthesis of a C16-C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spiroacetal moiety.

被引：58

作者：

Paterson, I

Wallace, DJ

Gibson, KR

机构：

[1] University Chemical Laboratory, Lensfield Road

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(97)10483-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-16-C-28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：8911 / 8914

页数：4

相关论文

共 17 条

[1] THE SPONGISTATINS, POTENTLY CYTOTOXIC INHIBITORS OF TUBULIN POLYMERIZATION, BIND IN A DISTINCT REGION OF THE VINCA DOMAIN [J].

BAI, RL ;

TAYLOR, GF ;

CICHACZ, ZA ;

HERALD, CL ;

KEPLER, JA ;

PETTIT, GR ;

HAMEL, E .

BIOCHEMISTRY, 1995, 34 (30) :9714-9721

[2]

BAI RL, 1993, MOL PHARMACOL, V44, P757

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].

BROWN, HC ;

RANDAD, RS ;

BHAT, KS ;

ZAIDLEWICZ, M ;

RACHERLA, US .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392

[4] A method for constructing the C2-C12 dispiroacetal moiety of altohyrtin A [J].

Claffey, MM ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7646-7647

[5]

Cowden C. J., 1997, ORG REACTIONS, V51, P1

[6] 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

[7] A method for constructing the C18-C28 dispiroacetal moiety of Altohyrtin A [J].

Hayes, CJ ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2678-2679

[8] CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].

JADHAV, PK ;

BHAT, KS ;

PERUMAL, PT ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439

[9]

Kobayashi M, 1996, CHEM PHARM BULL, V44, P2142

[10] A modular approach to marine macrolide construction .2. Concise stereocontrolled synthesis of the C17-C28 (CD) spiroacetal component [J].

Paquette, LA ;

Braun, A .

TETRAHEDRON LETTERS, 1997, 38 (29) :5119-5122