Synthetic studies on the rhizoxins .2. An approach to the C-10-C-26 subunit using ''substrate directed'' allylstannane additions to aldehydes.

被引:29
作者
Keck, GE
Savin, KA
Weglarz, MA
Cressman, ENK
机构
[1] Department of Chemistry, University of Utah, Salt Lake City
关键词
D O I
10.1016/0040-4039(96)00578-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The construction of a C-10-C-26 fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the requisite all E triene. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:3291 / 3294
页数:4
相关论文
共 31 条
[1]   SYNTHESIS OF THE LOWER SUBUNIT OF RHIZOXIN [J].
BOGER, DL ;
CURRAN, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2235-2244
[2]   ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS [J].
EVANS, DA ;
ANDREWS, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (05) :147-155
[3]   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
[4]  
IWASAKI S, 1989, NOVEL MICROBIAL PROD, P79
[5]   REGIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS USING THE MISLOW-EVANS REARRANGEMENT - A THEORETICAL RATIONALIZATION [J].
JONESHERTZOG, DK ;
JORGENSEN, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6682-6683
[6]   CHELATION CONTROLLED DIASTEREOFACIAL SELECTIVITY IN CROTYLTRI-N-BUTYLSTANNANE ADDITIONS TO ALPHA-ALKOXYALDEHYDES [J].
KECK, GE ;
BODEN, EP .
TETRAHEDRON LETTERS, 1984, 25 (18) :1879-1882
[7]   DIRECT EVIDENCE FOR THE ABSENCE OF CHELATION WITH BETA-SILYLOXY ALDEHYDES AND LEWIS-ACIDS [J].
KECK, GE ;
CASTELLINO, S .
TETRAHEDRON LETTERS, 1987, 28 (03) :281-284
[8]   USE OF SAMARIUM DIIODIDE AS AN ALTERNATIVE TO SODIUM MERCURY AMALGAM IN THE JULIA-LYTHGOE OLEFINATION [J].
KECK, GE ;
SAVIN, KA ;
WEGLARZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3194-3204
[9]   EFFECTS OF OLEFIN GEOMETRY ON THE STEREOCHEMISTRY OF LEWIS-ACID MEDIATED ADDITIONS OF CROTYLSTANNANES TO ALDEHYDES [J].
KECK, GE ;
SAVIN, KA ;
CRESSMAN, ENK ;
ABBOTT, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7889-7896
[10]   STEREOCHEMICAL CONSEQUENCES FOR THE LEWIS ACID MEDIATED ADDITIONS OF ALLYL AND CROTYLTRI-N-BUTYLSTANNANE TO CHIRAL BETA-HYDROXYALDEHYDE DERIVATIVES [J].
KECK, GE ;
ABBOTT, DE .
TETRAHEDRON LETTERS, 1984, 25 (18) :1883-1886