Unique trans-syn-cis [6.6.7] tricycle derivative from transannular Diels-Alder contraction of a model 15-membered trans-cis-cis macrocyclic triene

被引：1

作者：

Drouin, M ^{[1
]}

Hall, DG ^{[1
]}

Caille, AS ^{[1
]}

Deslongchamps, P ^{[1
]}

机构：

[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTH ORGAN LAB,SHERBROOKE,PQ J1K 2R1,CANADA

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | 1997年 / 53卷

关键词：

D O I：

10.1107/S0108270197005635

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A model 15-membered trans-cis-cis macrocyclic triene, (trans-cis-cis)-tetramethyl (4E, 11Z,13E)-5-formylcyclopentadeca-4,11,1 3-triene-1,1,8,8-tetracarboxylate, C-24-H32O9, was synthesized and led to the exclusive formation of a trans-syn-cis [6.6.7] tricyclic compound upon a transannular Diels-Alder reaction. The structure of the precursor and a p-bromobenzoyl analog of the product, (trans-syn-cis)-tetramethyl rac-(1S,2S,7R, 10R)-(8Z)-1-(4-bromobenzoyloxymethyl)tri cyclo[8.5.0.0(2,7)]pentadec-8-ene-5,5,13,13-tetracarboxylate ethanol solvate, 3C(31)H(37)BrO(10).0.76C(2)H(6)O, were determined in order to establish their exact geometries and ring-junction stereochemistries.

引用

页码：1490 / 1493

页数：4

共 14 条

[1] COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, C ;

GUAGLIARDI, A .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350

[2] STRUCTURE AND ABSOLUTE-CONFIGURATION OF ANTIBIOTIC APHIDICOLIN - TETRACYCLIC DITERPENOID CONTAINING A NEW RING-SYSTEM [J].

DALZIEL, W ;

HESP, B ;

STEVENSON, KM ;

JARVIS, JAJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (23) :2841-2851

[3] NRCVAX - AN INTERACTIVE PROGRAM SYSTEM FOR STRUCTURE-ANALYSIS [J].

GABE, EJ ;

LEPAGE, Y ;

CHARLAND, JP ;

LEE, FL ;

WHITE, PS .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :384-387

[4]

HALL DG, 1995, CAN J CHEM, P1695

[5]

HALL DG, 1995, CAN J CHEM, P1675

[6]

HALL DG, 1995, SYNTHESIS-STUTTGART, V9, P1081

[7] SCOPADULCIC ACID-A AND ACID-B, NEW DITERPENOIDS WITH A NOVEL SKELETON, FROM A PARAGUAYAN CRUDE DRUG TYPYCHA KURATU (SCOPARIA-DULCIS L) [J].

HAYASHI, T ;

KISHI, M ;

KAWASAKI, M ;

ARISAWA, M ;

SHIMIZU, M ;

SUZUKI, S ;

YOSHIZAKI, M ;

MORITA, N ;

TEZUKA, Y ;

KIKUCHI, T ;

BERGANZA, LH ;

FERRO, E ;

BASUALDO, I .

TETRAHEDRON LETTERS, 1987, 28 (32) :3693-3696

[8]

JOHNSON CK, 1995, XTAL GX

[9] TRANS-ANNULAR DIELS-ALDER REACTION OF 14-MEMBERED MACROCYCLIC TRIENES .1. THEORETICAL-ANALYSIS AND STEREOCHEMICAL PREDICTIONS [J].

LAMOTHE, S ;

NDIBWAMI, A ;

DESLONGCHAMPS, P .

TETRAHEDRON LETTERS, 1988, 29 (14) :1639-1640

[10]

Larson A.C., 1970, CRYSTALLOGRAPHIC COM, P291

← 1 2 →