Synthesis of alkaloid 223A and a structural revision

被引：58

作者：

Toyooka, N ^{[1
]}

Fukutome, A ^{[1
]}

Nemoto, H ^{[1
]}

Daly, JW ^{[1
]}

Spande, TF ^{[1
]}

Garraffo, HM ^{[1
]}

Kaneko, T ^{[1
]}

机构：

[1] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol025775m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Synthesis of alkaloid 223A has been achieved by sequential use of our original conjugate addition reaction to enaminoesters as the key step. The proposed structure for natural 223A (A, absolute configuration unknown) was revised to B, and the relative stereostructure was determined to be 5R*,6R*,8R*,9S* by the present synthesis.

引用

页码：1715 / 1717

页数：3

共 26 条

[1] PALLADIUM-CATALYZED CARBONYLATION OF ENOL TRIFLATES - A NOVEL METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES
CACCHI, S
MORERA, E
ORTAR, G
[J]. TETRAHEDRON LETTERS, 1985, 26 (08) : 1109 - 1112
[2] CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041
[3] Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A
Comins, DL
Huang, SL
McArdle, CL
Ingalls, CL
[J]. ORGANIC LETTERS, 2001, 3 (03) : 469 - 471
[4] Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B
Comins, DL
LaMunyon, DH
Chen, XH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) : 8182 - 8187
[5] PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES
COMINS, DL
DEHGHANI, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (42) : 6299 - 6302
[6] A SHORT, STEREOSPECIFIC ROUTE TO CHIRAL TRANS-2,6-DISUBSTITUTED QUINUCLIDINES
COREY, EJ
YUEN, PW
[J]. TETRAHEDRON LETTERS, 1989, 30 (43) : 5825 - 5828
[7] Daly J. W, 1998, The Alkaloids: Chemistry and Biology, V50, P141, DOI 10.1016/S1099-4831(08)60042-5
[8] Daly JW, 1999, ALKAL CHEM, V13, P1, DOI 10.1016/S0735-8210(99)80024-7
[9] Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
Chao, B
Rao, A
[J]. ORGANIC LETTERS, 2001, 3 (20) : 3169 - 3171
[10] Enders D, 2000, SYNLETT, P1745

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