Total synthesis of (+)-crocacin C

被引：53

作者：

Dias, LC ^{[1
]}

de Oliveira, LG ^{[1
]}

机构：

[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 24期

关键词：

D O I：

10.1021/ol016845c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.

引用

页码：3951 / 3954

页数：4

共 29 条

[1]

BRABANDER JD, 1994, SYNTHESIS-STUTTGART, P855

[2]

Chakraborty TK, 2001, TETRAHEDRON LETT, V42, P497, DOI 10.1016/S0040-4039(00)02002-5

[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] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[5] The intramolecular Stille reaction [J].

Duncton, MAJ ;

Pattenden, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1235-1246

[6]

Evans D. A., 1989, ORG SYNTH, V68, P83

[7] ENANTIOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES - A STERIC MODEL FOR ASYMMETRIC INDUCTION [J].

EVANS, DA ;

TABER, TR .

TETRAHEDRON LETTERS, 1980, 21 (49) :4675-4678

[8] DIASTEREOSELECTIVE ANTIALDOL REACTIONS OF CHIRAL ETHYL KETONES - ENANTIOSELECTIVE PROCESSES FOR THE SYNTHESIS OF POLYPROPIONATE NATURAL-PRODUCTS [J].

EVANS, DA ;

NG, HP ;

CLARK, JS ;

RIEGER, DL .

TETRAHEDRON, 1992, 48 (11) :2127-2142

[9] C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].

EVANS, DA ;

RIEGER, DL ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100

[10] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

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