STEREOCONTROLLED SYNTHESIS OF ISOCOMENE BY A NOVEL PHOTOCYCLOADDITION-FRAGMENTATION STRATEGY

被引:28
作者
RAWAL, VH
DUFOUR, C
ESCHBACH, A
机构
关键词
D O I
10.1039/c39940001797
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isocomene has been synthesized in a stereocontrolled manner by a novel strategy that utilizes a Paterno-Buchi reaction to build complexity and a selective reductive fragmentation to reveal a functionalized diquinane.
引用
收藏
页码:1797 / 1798
页数:2
相关论文
共 35 条
[1]   NATURALLY OCCURRING DERIVATIVES .108. ANOMAL SESQUITERPENE FROM BERKHEYA-RADULA (HARV) DE WILLD [J].
BOHLMANN, F ;
LEVAN, N ;
PICKARDT, J .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (12) :3777-3781
[2]   SYNTHETICALLY USEFUL BETA-LITHIOALKOXIDES FROM REDUCTIVE LITHIATION OF EPOXIDES BY AROMATIC RADICAL-ANIONS [J].
COHEN, T ;
JEONG, IH ;
MUDRYK, B ;
BHUPATHY, M ;
AWAD, MMA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1528-1536
[3]   PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES [J].
COMINS, DL ;
DEHGHANI, A .
TETRAHEDRON LETTERS, 1992, 33 (42) :6299-6302
[4]   STEREOCHEMISTRY OF METAL HALOGEN EXCHANGE-INITIATED INTRAMOLECULAR CONJUGATE ADDITION-REACTIONS IN THE CONSTRUCTION OF 5-MEMBERED CARBOCYCLES [J].
COOKE, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1495-1503
[5]   METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1345-+
[6]   FORMAL TOTAL SYNTHESIS OF (+1-)-ISOCOMENE [J].
DAUBEN, WG ;
WALKER, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1103-1108
[7]   POLYSPIRANES .17. CASCADE REARRANGEMENTS .12. (+/-)MODHEPHENE AND (+/-)ISOCOMENE VIA CASCADE REARRANGEMENT [J].
FITJER, L ;
KANSCHIK, A ;
MAJEWSKI, M .
TETRAHEDRON LETTERS, 1988, 29 (43) :5525-5528
[8]   ALKYLLITHIUM REAGENTS FROM ALKYL-HALIDES AND LITHIUM RADICAL-ANIONS [J].
FREEMAN, PK ;
HUTCHINSON, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1924-1930
[9]   APPROACH TO THE TOTAL SYNTHESIS OF CHLOROTHRICOLIDE - SYNTHESIS OF (+/-)-19,20-DIHYDRO-24-O-METHYLCHLOROTHRICOLIDE, METHYL-ESTER, ETHYL CARBONATE [J].
IRELAND, RE ;
VARNEY, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :635-648
[10]   STEREOSPECIFIC TOTAL SYNTHESIS OF 9-AMINOANTHRACYCLINES - (+)-9-AMINO-9-DEOXYDAUNOMYCIN AND RELATED-COMPOUNDS [J].
ISHIZUMI, K ;
OHASHI, N ;
TANNO, N .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4477-4485