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Titolo:
A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)-coronafacic acid and a formal synthesis of (+)-coriolin
Autore:
Mehta, G; Reddy, DS;
Indirizzi:
Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India Univ Hyderabad Hyderabad Andhra Pradesh India 500046 ndhra Pradesh, India Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India Indian Inst Sci Bangalore Karnataka India 560012 560012, Karnataka, India
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 10, , anno: 2001,
pagine: 1153 - 1161
SICI:
1472-7781(2001):10<1153:ASEIEH>2.0.ZU;2-P
Fonte:
ISI
Lingua:
ENG
Soggetto:
FUNCTIONALIZED CIS-HYDRINDANES; TANDEM WESSELY OXIDATION; HALLER-BAUER CLEAVAGE; (+/-)-CORONAFACIC ACID; ABSOLUTE-CONFIGURATION; NATURAL-PRODUCTS; REARRANGEMENT; OXAZIRIDINES; CONSTRUCTION; RESOLUTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
59
Recensione:
Indirizzi per estratti:
Indirizzo: Mehta, G Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, IndiaUniv Hyderabad Hyderabad Andhra Pradesh India 500046 desh, India
Citazione:
G. Mehta e D.S. Reddy, "A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)-coronafacic acid and a formal synthesis of (+)-coriolin", J CHEM S P1, (10), 2001, pp. 1153-1161

Abstract

A ready access to enantiopure 3,10-dioxygenated tricyclo[5.2.1.0(2,6)]decane derivatives is reported. An efficient enzymatic kinetic resolution is employed through transesterification in the presence of lipase PS immobilizedon Celite. Absolute configuration of the tricyclo[5.2.1.0(2,6)]decan-10-one derivatives has been secured through correlation with (1R,2S)-1-aminoindan-2-ol. The promising utility of these enantiopure tricyclo[5.2.1.0(2,6)]decane derivatives in synthesis has been demonstrated through the preparationof several optically pure cis-hydrindanes 15-18, employing the Haller-Bauer reaction as the key step for unbridging the trinorbornyl system. The cis-hydrindane (-)-16 has been further elaborated to the natural product (+)-coronafacic acid (+)-24. In an interesting sequence, cis-hydrindanone (+)-18 has been transformed into cis-hydroisoquinolones (+)-30 and (+)-33 via photorearrangement of the derived oxaziridines 29 and 32, respectively. The hydroisoquinolones (+)-30 and (+)-33 can serve as useful enantiopure building blocks for the synthesis of complex indole alkaloids. Oxidative cleavage ofthe trinorbornene double bond in the tricyclo[5.2.1.0(2,6)]decan-10-one derivative (-)-37 and functional-group adjustments leads to the optically pure diquinane (+)-38, an advanced intermediate in the total synthesis of (+)-coriolin (+)-34.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/03/20 alle ore 10:42:20