Condensed cyclic and bridged-ring systems-14. stnthesis of some bridged propano-hydrophenanthrene, -hydrofluorene and polycyclic benzo-propellane derivatives through intramolecular c-alkylations of γ δ-unsaturated α'-diazomethyl ketones

Ray, Chhanda; Saha, Bijali; Ghatak, Usha Ranjan

doi:10.1016/s0040-4020(01)88378-2

Cited by 5 publications

(1 citation statement)

References 21 publications

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“…Initial attempts to effect the cyclization of α-diazoketone 19 , Rh 2 (OAc) 4 , BF 3 ·OEt 2 , trifluoroacetic acid/HClO 4 , and HClO 4 , all gave disappointing results. Eventually, the desired intramolecular insertion was successfully carried out by a slow addition of diazoketone 19 over a refluxing solution of bis( N - tert -butylsalicylaldiminato)copper(II) (BTBSACu) in toluene to give ketone 20 in 82% yield.…”

Section: Resultsmentioning

confidence: 99%

First Diastereoselective Synthesis of (−)-Methyl Thyrsiflorin A, (−)-Methyl Thyrsiflorin B Acetate, and (−)-Thyrsiflorin C

et al. 2000

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An efficient procedure for the synthesis of scopadulan diterpenes, using (+)-podocarp-8(14)-en-13-one 13 as starting material, is reported. This procedure has been used for the diastereoselective synthesis of (-)-methyl thyrsiflorin A (8), (-)-methyl thyrsiflorin B acetate (9), and (-)-thyrsiflorin C (7). Key steps in our strategy are the intramolecular cyclopropanation of diazoketone 19 and the regioselective cleavage of the cyclopropane ring.

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Section: Resultsmentioning

confidence: 99%

First Diastereoselective Synthesis of (−)-Methyl Thyrsiflorin A, (−)-Methyl Thyrsiflorin B Acetate, and (−)-Thyrsiflorin C

et al. 2000

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ChemInform Abstract: Condensed Cyclic and Bridged‐Ring Systems. Part 14. Synthesis of Some Bridged Propanohydrophenanthrene, ‐hydrofluorene and Polycyclic Benzopropellane Derivatives Through Intramolecular C‐Alkylations of γ,δ‐Unsaturated α′‐Diazomethyl Ketones.

Ray¹,

Saha²,

Ghatak³

1990

ChemInform

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ChemInform Abstract The access to a variety of title compounds such as the propanohydrophenanthrene (III) and the benzopropellane (IV) is achieved via intramolecular keto-carbenoid addition of the diazopropanone (I) and subsequent regiospecific reductive cleavage of the cyclopropyl ketone (II). A similar procedure starting with the diazopropanone (V) leads to the corresponding hydrofluorene derivatives. The cyclopropyl ketone (VI) undergoes an interesting rearrangement to give the cyclohexenone (VII). The novel bridged hydrocarbons possess structures related to the powerful insect attractant (±)-9a-carbomorphinan (VIII).

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Application of Intramolecular Carbenoid Reactions in Organic Synthesis

1992

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Condensed cyclic and bridged-ring systems-14. stnthesis of some bridged propano-hydrophenanthrene, -hydrofluorene and polycyclic benzo-propellane derivatives through intramolecular c-alkylations of γ δ-unsaturated α'-diazomethyl ketones

Cited by 5 publications

References 21 publications

First Diastereoselective Synthesis of (−)-Methyl Thyrsiflorin A, (−)-Methyl Thyrsiflorin B Acetate, and (−)-Thyrsiflorin C

First Diastereoselective Synthesis of (−)-Methyl Thyrsiflorin A, (−)-Methyl Thyrsiflorin B Acetate, and (−)-Thyrsiflorin C

ChemInform Abstract: Condensed Cyclic and Bridged‐Ring Systems. Part 14. Synthesis of Some Bridged Propanohydrophenanthrene, ‐hydrofluorene and Polycyclic Benzopropellane Derivatives Through Intramolecular C‐Alkylations of γ,δ‐Unsaturated α′‐Diazomethyl Ketones.

Application of Intramolecular Carbenoid Reactions in Organic Synthesis

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