A convenient synthesis of A-ring-functionalized podolactones. Revision of the structure of wentilactone B

被引：20

作者：

Barrero, AF ^{[1
]}

Herrador, MM ^{[1
]}

del Moral, JFQ ^{[1
]}

Valdivia, MV ^{[1
]}

机构：

[1] Univ Granada, Inst Biotechnol, Dept Organ Chem, E-18071 Granada, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 08期

关键词：

D O I：

10.1021/ol0257070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new route to podolactones functionalized in the A ring has been achieved. Two key steps were employed in this synthesis, the construction of the bicyclic skeleton via a Mn(III)-mediated radical cyclization and the transformation of this bicyclic intermediate into the tetracyclic podolactone skeleton through a Pd (II)-mediated bislactonization of the corresponding conjugate diene. The reported synthesis of 3beta-hydroxy-13,14,15,16-tetranorlabda-7,9(11)-dien-(19,6beta),(12,17)-diolide (1) let us reassign the structure of wentilactone B, for which structure 1 was wrongly reported.

引用

页码：1379 / 1382

页数：4

共 28 条

[1]

BACKVALL JE, 1993, J ORG CHEM, V58, P5445

[2]

BACKVALL JE, 1984, J ORG CHEM, V49, P4619

[3]

Backvall JE, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P339

[4] Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction.: Synthesis of oidiolactone C [J].

Barrero, AF ;

Del Moral, JFQ ;

Cuerva, JM ;

Cabrera, E ;

Jiménez-González, D .

TETRAHEDRON LETTERS, 2000, 41 (27) :5203-5206

[5] A new strategy for the synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes [J].

Barrero, AF ;

Cuerva, JM ;

Herrador, MM ;

Valdivia, MV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4074-4078

[6]

BARRERO AF, 2002, IN PRESS J ORG CHEM

[7]

COATES RM, 1999, HDB REAGENTS ORGANIC, P180

[8]

COREY EJ, 1972, TETRAHEDRON LETT, V13, P5203

[9] ISOLATION AND IDENTIFICATION OF 2 NEW BIOLOGICALLY-ACTIVE NORDITERPENE DILACTONES FROM ASPERGILLUS-WENTII [J].

DORNER, JW ;

COLE, RJ ;

SPRINGER, JP ;

COX, RH ;

CUTLER, H ;

WICKLOW, DT .

PHYTOCHEMISTRY, 1980, 19 (06) :1157-1161

[10] STRUCTURE AND CHEMISTRY OF ANTIBIOTIC LL-Z1271 ALPHA, AN ANTIFUNGAL C-17 TERPENE [J].

ELLESTAD, GA ;

EVANS, RH ;

KUNSTMANN, MP ;

LANCASTER, JE ;

MORTON, GO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5483-+

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