A novel one-pot annelation, decarboxylation reaction: synthesis of (±)- trans -benzohydrindane

Ravindranathan, T.; Patil, Sachindra S.; Pai, Ganesh G.

doi:10.1016/s0040-4039(02)00131-4

Cited by 3 publications

(1 citation statement)

References 31 publications

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“…In addition, they have been reported to exhibit a remarkable hormonal and anti‐hormonal activity,2 and to have modulatory actions at GABA A receptors as neurosteroid analogues 3. For the synthesis of these compounds, the development of a method to construct the trans ‐4,5‐benzhydrindane skeleton ( 1 ; Figure 1)4 as an enantiopure form is a critical and essential task. However, a truly effective approach for this purpose has not been reported so far, although several efforts have been made, including ours 5.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of A‐Nor B‐Aromatic OSW‐1 Aglycon: A Highly Effective Approach to Optically Active trans‐4,5‐Benzhydrindane

Matsuya¹,

Itoh²,

Nemoto³

2003

Eur J Org Chem

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of A‐Nor B‐Aromatic OSW‐1 Aglycon: A Highly Effective Approach to Optically Active trans‐4,5‐Benzhydrindane

Matsuya¹,

Itoh²,

Nemoto³

2003

Eur J Org Chem

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A Practical Asymmetric Synthesis of trans-4,5-Benzhydrindan-1-ones as a Precursor of A-Nor B-Aromatic Steroidal Compounds

et al. 2005

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The enantio-controlled synthesis of trans-4,5-benzhydrindan-1-ones was achieved by means of a stereoselective [4+2] cycloaddition of o-quinodimethanes generated by a thermal cleavage of benzocyclobutene derivatives as a key step. The chiral substrates of the thermal reaction were synthesized by a diastereoselective Grignard addition to the chiral O-isopropylideneglyceroketones connected to a benzocyclobutene ring, which were simply prepared from D-mannitol as a chiral source. This approach can provide a new efficient access to A-nor B-aromatic steroidal compounds.

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Crystal structures and Hirshfeld surface analyses of a des-A-B-aromatic steroidal compound, and two of its derivatives, having a trans-2,3,4,5-tetrahydro-3a-methyl-7-methoxybenz[e]indane skeleton – structural comparisons with reported tetrahydrobenz[e]indene derivatives

Gomes

Low

Turner

et al. 2019

Zeitschrift Für Naturforschung B

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The crystal structures and Hirshfeld surface analyses of the des-A-B-aromatic steroid derivative, (3a,9b)-1,2,3a,4,5,9b-hexahydro-7-methoxy-3a-methyl-3H-benz[e]-inden-3-one (or 5-methoxy-des-A-estra-5,7,9-triene-17-one) 1, its acetohydrazide derivative, 2, and its hydrazone derivative, 3, are reported. All three compounds crystallize in chiral space groups: compounds 1 and 2 in the orthorhombic space group P212121 each with one molecule in the asymmetric unit, and compound 3 in the monoclinic space group P21 with two similar but independent molecules, Mol A and Mol B, in the asymmetric unit. Both the five-membered and six-membered non-aromatic rings in all three compounds have envelope or near envelope shapes. In compounds 2 and 3 the N=N units have (E)-arrangements. The intermolecular interactions in crystals of compound 1 are C–H · · · O hydrogen bonds and C–H · · · π interactions, in compound 2 N–H · · · O and C–H · · · O hydrogen bonds and C–H · · · π interactions are present, while in compound 3 there are just C–H · · · π interactions. An important substructure in 1 is a sheet of molecules, composed of ${\rm{R}}_6^6(44)$ rings, formed from C–H · · · O(methoxy) and C–H · · · O(carbonyl) hydrogen bonds, the molecules of which form columns linked via the B and D rings, i.e. in a head-to-tail fashion. Compound 2 is an acylhydrazonyl compound, in which the two independent molecules are linked into asymmetric dimers via strong classical N–H · · · O hydrogen bonds, with the formation of ${\rm{R}}_2^2(8)$ rings. In both 1 and 2, further intermolecular interactions result in 3-dimensional structures, while compound 3 has a 1-dimensional structure arising from C–H · · · O interactions generating spiral chains. The results have been compared with existing data.

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A novel one-pot annelation, decarboxylation reaction: synthesis of (±)- trans -benzohydrindane

Cited by 3 publications

References 31 publications

Total Synthesis of A‐Nor B‐Aromatic OSW‐1 Aglycon: A Highly Effective Approach to Optically Active trans‐4,5‐Benzhydrindane

Total Synthesis of A‐Nor B‐Aromatic OSW‐1 Aglycon: A Highly Effective Approach to Optically Active trans‐4,5‐Benzhydrindane

A Practical Asymmetric Synthesis of trans-4,5-Benzhydrindan-1-ones as a Precursor of A-Nor B-Aromatic Steroidal Compounds

Crystal structures and Hirshfeld surface analyses of a des-A-B-aromatic steroidal compound, and two of its derivatives, having a trans-2,3,4,5-tetrahydro-3a-methyl-7-methoxybenz[e]indane skeleton – structural comparisons with reported tetrahydrobenz[e]indene derivatives

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