Spongistatin synthetic studies .1. Construction of a C(29-48) subtarget

被引:67
作者
Smith, AB [1 ]
Zhuang, LH [1 ]
Brook, CS [1 ]
Boldi, AM [1 ]
McBriar, MD [1 ]
Moser, WH [1 ]
Murase, N [1 ]
Nakayama, K [1 ]
Verhoest, PR [1 ]
Lin, QY [1 ]
机构
[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)10499-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this Letter, the first in a series of three, we outline our overall strategy and describe the assembly of a C(29-48) EF-ring advanced intermediate for the total synthesis of the spongistatins, rare and structurally unique polyether macrolides with unprecedented antitumor activity. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8667 / 8670
页数:4
相关论文
共 28 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]   CARBONATE EXTENSION - A VERSATILE PROCEDURE FOR FUNCTIONALIZATION OF ACYCLIC HOMOALLYLIC ALCOHOLS WITH MODERATE STEREOCONTROL [J].
BARTLETT, PA ;
MEADOWS, JD ;
BROWN, EG ;
MORIMOTO, A ;
JERNSTEDT, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4013-4018
[3]   SYNTHESIS OF BRYOSTATINS .1. CONSTRUCTION OF THE C(1)-C(16) FRAGMENT [J].
BLANCHETTE, MA ;
MALAMAS, MS ;
NANTZ, MH ;
ROBERTS, JC ;
SOMFAI, P ;
WHRITENOUR, DC ;
MASAMUNE, S ;
KAGEYAMA, M ;
TAMURA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2817-2825
[5]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[6]   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
[7]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[8]  
DELIMA C, 1992, SYNLETT, P133
[9]   IODINE MONOBROMIDE (IBR) AT LOW-TEMPERATURE - ENHANCED DIASTEREOSELECTIVITY IN ELECTROPHILIC CYCLIZATIONS OF HOMOALLYLIC CARBONATES [J].
DUAN, JJW ;
SMITH, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3703-3711
[10]   BIOACTIVE MARINE METABOLITES .48. CINACHYROLIDE-A - A POTENT CYTOTOXIC MACROLIDE POSSESSING 2 SPIRO KETALS FROM MARINE SPONGE CINACHYRA SP [J].
FUSETANI, N ;
SHIMODA, K ;
MATSUNAGA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3977-3981