Studies on the total synthesis of the macrolide antitumor agent rhizoxin .2. Synthesis of the C14-C26 segment.

被引：23

作者：

White, JD

Holoboski, MA

Green, NJ

机构：

[1] Department of Chemistry, Oregon State University, Corvallis

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 42期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(97)01781-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of the C14-C26 segment of rhizoxin as described in which the three stereogenic centers are derived from a gamma-lactone; stannylcupration-methylation of a terminal alkyne is used to generate an (E)-iodoalkene for Stille coupling with a dienylstannane that produces the conjugated (E,E,E)-triene unit of rhizoxin. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：7333 / 7336

页数：4

相关论文

共 25 条

[1] SYNTHESIS OF THE LOWER SUBUNIT OF RHIZOXIN [J].

BOGER, DL ;

CURRAN, TT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2235-2244

[2] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[3] 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

[4]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[5] ELABORATION OF ALDEHYDES AND KETONES TO ALKYNES - IMPROVED METHODOLOGY [J].

GILBERT, JC ;

WEERASOORIYA, U .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4997-4998

[6] STEREOCHEMICAL CONTROL OF NATURES BIOSYNTHETIC PATHWAYS - A GENERAL STRATEGY FOR THE SYNTHESIS OF POLYPROPIONATE-DERIVED STRUCTURAL UNITS FROM A SINGLE CHIRAL PROGENITOR [J].

HANESSIAN, S ;

MURRAY, PJ .

TETRAHEDRON, 1987, 43 (21) :5055-5072

[7]

Harris L, 1996, SYNLETT, P903

[8] PRECLINICAL ANTITUMOR-ACTIVITY AND ANIMAL TOXICOLOGY STUDIES OF RHIZOXIN, A NOVEL TUBULIN-INTERACTING AGENT [J].

HENDRIKS, HR ;

PLOWMAN, J ;

BERGER, DP ;

PAULL, KD ;

FIEBIG, HH ;

FODSTAD, O ;

DREEFVANDERMEULEN, HC ;

HENRAR, REC ;

PINEDO, HM ;

SCHWARTSMANN, G .

ANNALS OF ONCOLOGY, 1992, 3 (09) :755-763

[9] STUDIES ON MACROCYCLIC LACTONE ANTIBIOTICS .8. ABSOLUTE STRUCTURES OF RHIZOXIN AND A RELATED COMPOUND [J].

IWASAKI, S ;

NAMIKOSHI, M ;

KOBAYASHI, H ;

FURUKAWA, J ;

OKUDA, S ;

ITAI, A ;

KASUYA, A ;

IITAKA, Y .

JOURNAL OF ANTIBIOTICS, 1986, 39 (03) :424-429

[10] STUDIES ON MACROCYCLIC LACTONE ANTIBIOTICS .7. STRUCTURE OF A PHYTOTOXIN RHIZOXIN PRODUCED BY RHIZOPUS-CHINENSIS [J].

IWASAKI, S ;

KOBAYASHI, H ;

FURUKAWA, J ;

NAMIKOSHI, M ;

OKUDA, S ;

SATO, Z ;

MATSUDA, I ;

NODA, T .

JOURNAL OF ANTIBIOTICS, 1984, 37 (04) :354-362