Optically active cyclobutanone chemistry:: Synthesis of (-)-cyclobut-A and (±)-3′-epi-cyclobut-A

被引：46

作者：

Brown, B ^{[1
]}

Hegedus, LS ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 22期

关键词：

D O I：

10.1021/jo9817063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The carbocyclic nucleoside analogues (-)-cyclobut-A and (+/-)-3'-epi-cyclobut-A were synthesized utilizing photolysis of the (benzyloxymethyl)(methoxy) chromium carbene complex 4 with optically active ene-carbamate 5 to produce the corresponding optically active alpha,alpha-disubstituted cyclobutanone 6. Stereoselective removal of the alpha-ethoxy group with inversion gave cyclobutanone 7, which was converted by existing methodology to the title compounds.

引用

页码：8012 / 8018

页数：7

共 35 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES
AGROFOGLIO, L
SUHAS, E
FARESE, A
CONDOM, R
CHALLAND, SR
EARL, RA
GUEDJ, R
[J]. TETRAHEDRON, 1994, 50 (36) : 10611 - 10670
[2] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS
BELLUS, D
ERNST, B
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06): : 797 - 827
[3] REGIOSELECTIVE COUPLING OF TETRAALKYLAMMONIUM SALTS OF 6-IODO-2-AMINOPURINE TO A CYCLOBUTYL TRIFLATE - EFFICIENT PREPARATION OF HOMOCHIRAL BMS-180,194, A POTENT ANTIVIRAL CARBOCYCLIC NUCLEOSIDE
BISACCHI, GS
SINGH, J
GODFREY, JD
KISSICK, TP
MITT, T
MALLEY, MF
DIMARCO, JD
GOUGOUTAS, JZ
MUELLER, RH
ZAHLER, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) : 2902 - 2905
[4] BISSACHI GS, 1991, J MED CHEM, V34, P1415
[5] PALLADIUM(II)-CATALYZED RING EXPANSION OF METHYLENECYCLOBUTANES AND RELATED SYSTEMS
BOONTANONDA, P
GRIGG, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (17) : 583 - 584
[6] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES
BORTHWICK, AD
BIGGADIKE, K
[J]. TETRAHEDRON, 1992, 48 (04) : 571 - 623
[7] Synthesis and reactivity of optically active spiroketals by ring-expansion of chromium carbene complex-derived cyclobutanones
Bueno, AB
Hegedus, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) : 684 - 690
[8] CHEMOENZYMATIC SYNTHESIS OF CARBOCYCLIC OXETANOCIN-A INVOLVING A NOVEL PHOTOCHEMICAL-REARRANGEMENT
COTTERILL, IC
ROBERTS, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20): : 2585 - 2586
[9] RHODIUM(I)-CATALYZED AND IRIDIUM(I)-CATALYZED HYDROBORATION REACTIONS - SCOPE AND SYNTHETIC APPLICATIONS
EVANS, DA
FU, GC
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) : 6671 - 6679
[10] A FACILE CONVERSION OF SUBSTITUTED CYCLOBUTANONES TO CYCLOPENTANONES BY CH2I2/SMI2 SYSTEM
FUKUZAWA, S
TSUCHIMOTO, T
[J]. TETRAHEDRON LETTERS, 1995, 36 (33) : 5937 - 5938

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