Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline

被引：23

作者：

Drutu, I ^{[1
]}

Krygowski, ES ^{[1
]}

Wood, JL ^{[1
]}

机构：

[1] Yale Univ, Sterling Chem Lab, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo015741c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a short, enantioselective synthesis of the naturally occurring pyrrolizidine alkaloid (+)-latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key step in constructing (+)-latifolic acid (4).

引用

页码：7025 / 7029

页数：5

共 20 条

[1] DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].

BAUM, JS ;

SHOOK, DA ;

DAVIES, HML ;

SMITH, HD .

SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1709-1716

[2] TETRAFLUOROSILANE IS A MILD AND VERY SELECTIVE REAGENT FOR THE CLEAVAGE OF SILYL-PROTECTED ALCOHOLS [J].

COREY, EJ ;

YI, KY .

TETRAHEDRON LETTERS, 1992, 33 (17) :2289-2290

[3] ALKALOIDS OF CYNOGLOSSUM LATIFOLIUM RBR LATIFOLINE AND 7-ANGELYLRETRONECINE [J].

CROWLEY, HC ;

CULVENOR, CC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1962, 15 (01) :139-&

[4] PYRROLIZIDINE ALKALOID ANALOGS - PREPARATION OF SEMISYNTHETIC ESTERS OF RETRONECINE [J].

HOSKINS, WM ;

CROUT, DHG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05) :538-544

[5]

LEY SV, 1994, SYNTHESIS-STUTTGART, P639

[6] Enantioselective synthesis of senecivernine, a 12-membered dilactonic pyrrolizidine alkaloid [J].

Liu, ZY ;

Zhao, LY .

TETRAHEDRON LETTERS, 1999, 40 (30) :5593-5596

[7] PYRROLIZIDINE ALKALOIDS - ABSOLUTE-CONFIGURATIONS OF LATIFOLIC ACID AND ITS STEREOISOMERS [J].

MATSUMOTO, T ;

OKABE, T ;

FUKUI, K .

CHEMISTRY LETTERS, 1973, (08) :773-776

[8] SENECIO ALKALOIDS - SYNTHESIS AND CONFIGURATION OF +/-LATIFOLIC ACID [J].

MATSUMOTO, T ;

FUKUI, K ;

OKABE, T .

CHEMISTRY LETTERS, 1972, (01) :29-+

[9]

MCKILLOP A, 1979, SYNTHESIS-STUTTGART, P401

[10] TOTAL SYNTHESIS OF A MACROCYCLIC PYRROLIZIDINE ALKALOID, (+/-)-INTEGERRIMINE, UTILIZING AN ACTIVABLE PROTECTING GROUP [J].

NARASAKA, K ;

SAKAKURA, T ;

UCHIMARU, T ;

GUEDINVUONG, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2954-2961

← 1 2 →