ChemInform Abstract: SYNTHESIS OF INDOLES CONDENSED WITH A BICYCLO(3.3.1)NONANE SKELETON

Kadzyauskas, P. P.; Butkus, Eugenijus; Vasyulite, Yu. A.; Averina, N. V.; Зефиров, Н. С.

doi:10.1002/chin.197932249

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“…The search for chiral molecules with the indole ring in a well-defined spatial orientation leads to the structure of an indole ring fused with an alicyclic framework. The construction of racemic compounds containing indole rings fused with bicyclo[3.3.1]nonanes has been accomplished earlier through the reaction of the corresponding 2,6-dione 1 with phenylhydrazine under the Fisher cyclization reaction conditions . Therefore, the synthesis and the study of the enantiomeric molecules in which both structural fragments are available became a challenge.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of methanocycloocta[b]indoles has been reported to be realized through the reaction of a (()-dione 1 with phenylhydrazine via intermediate hydrazone formation. 11 In this work the synthesis of the corresponding chiral structures was accomplished by an application of this methodology using enantiomerically enriched starting dione 1 (Scheme 1). The reaction of (-)-(1R,5R)dione 1 with phenylhydrazine in the presence of hydrochloric acid gave bishydrazone at room temperature.…”

Section: Synthesis Of Enantiomeric Methanocyclocta[b]indoles From Opt...mentioning

confidence: 99%

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Synthesis and Chiroptical Properties of Methanocycloocta[b]indoles

et al. 2000

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The synthesis of chiral methanocyclocta[b]indoles, the fused structures obtained from enantiomeric bicyclo[3.3.1]nonanones via Fisher indolization reaction, is reported. The starting optically active bicyclo[3.3.1]nonane-2,6-dione (1) was obtained by a chiral HPLC enantiomer separation on a swollen microcrystalline triacetylcellulose column and by the enzymatic resolution of the racemic dione. The circular dichroism (CD) spectra of the chiral structures 4, 5, and 7 were recorded, and the absolute configuration for the indole compounds was assigned. The theoretical calculations of the CD spectrum of diindole 4 reproduce the (1)B(b) couplet at 229 nm but predict wrong signs for the (1)L(a) and (1)L(b) bands using standard polarization directions. The CD spectrum of indole ketone 5 is reproduced correctly.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Enantiomeric Methanocyclocta[b]indoles From Opt...mentioning

confidence: 99%