Spongistatin synthetic studies .3. Construction of the C(1-17) spiroketal

被引：52

作者：

Smith, AB ^{[1
]}

Lin, QY ^{[1
]}

Nakayama, K ^{[1
]}

Boldi, AM ^{[1
]}

Brook, CS ^{[1
]}

McBriar, MD ^{[1
]}

Moser, WH ^{[1
]}

Sobukawa, M ^{[1
]}

Zhuang, LH ^{[1
]}

机构：

[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 50期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)10501-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent synthesis of the C(1-17) AB-ring subunit of the spongistatins, exceedingly scarce and highly antimitotic polyether macrolides, has been achieved via a one-flask dithiane bisalkylation, stereocontrolled spiroketalization, and Julia sulfone coupling/methylenation. (C) 1997 Elsevier Science Ltd.

引用

页码：8675 / 8678

页数：4

共 27 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] 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

[3] 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

[4] A CONVERGENT GENERAL SYNTHETIC PROTOCOL FOR CONSTRUCTION OF SPIROCYCLIC KETAL IONOPHORES - AN APPLICATION TO THE TOTAL SYNTHESIS OF (-)-A-23187 (CALCIMYCIN) [J].

BOECKMAN, RK ;

CHARETTE, AB ;

ASBEROM, T ;

JOHNSTON, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7553-7555

[5] NEW MOLECULAR MECHANICS (MM2) PARAMETERS FOR KETONES AND ALDEHYDES [J].

BOWEN, JP ;

PATHIASERIL, A ;

PROFETA, S ;

ALLINGER, NL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5162-5166

[6] B-ALLYLDIISOPINOCAMPHEYLBORANE - A REMARKABLE REAGENT FOR THE DIASTEREOSELECTIVE ALLYLBORATION OF ALPHA-SUBSTITUTED CHIRAL ALDEHYDES [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :319-320

[7] A HIGHLY DIASTEREOSELECTIVE ADDITION OF (E)-CROTYLDIISOPINOCAMPHEYLBORANES AND (Z)-CROTYLDIISOPINOCAMPHEYLBORANES TO ALPHA-SUBSTITUTED ALDEHYDES [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3701-3702

[8] 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

[9] REGIOSELECTIVE TITANIUM MEDIATED REDUCTIVE OPENING OF 2,3-EPOXY ALCOHOLS [J].

DAI, LX ;

LOU, BL ;

ZHANG, YZ ;

GUO, GZ .

TETRAHEDRON LETTERS, 1986, 27 (36) :4343-4346

[10] 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

← 1 2 3 →