9,10-dimethylenetricyclo[5.3.0.02,8]deca-3,5-diene

Paquette, Leo A.; Dressel, J.; Pansegrau, Paul D.

doi:10.1016/s0040-4039(00)96671-1

Cited by 23 publications

(2 citation statements)

References 16 publications

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“…A number of different oxidants were available for this purpose . We initially decided to use RuO 2 as our oxidizing agent. , In our hands, this oxidizing system gave very poor results. The major products of this reaction appeared to be the corresponding aldehyde, which showed considerable decomposition in the aromatic region of the 1 H NMR spectra of the crude product.…”

Section: Resultsmentioning

confidence: 99%

Aziridine−Allylsilane-Mediated Total Synthesis of (−)-Yohimbane

Bergmeier

Seth

1999

J. Org. Chem.

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A total asymmetric synthesis of (-)-yohimbane and ent-alloyohimbane is reported. The synthesis utilizes a novel aziridine-allylsilane cyclization reaction as a key step in the synthesis. Treatment of optically pure aziridine-allylsilane 16 with BF(3).OEt(2) provided a mixture of aminomethyl substituted carbocycles trans-20a and cis-20b in excellent yield and modest diastereoselectivity (trans/cis 3:1). Alkylation of the tosylamide followed by oxidation of the olefin in 20 provided the lactam 38, which was converted to (-)-yohimbane and ent-alloyohimbane by a Bischler-Napieralski reaction. The synthesis provided (-)-yohimbane in eight steps and 24% overall yield (from 16).

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Section: Resultsmentioning

confidence: 99%

Aziridine−Allylsilane-Mediated Total Synthesis of (−)-Yohimbane

Bergmeier

Seth

1999

J. Org. Chem.

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“…This substance, the first square-planar d10 organometallic complex known, is stable to heat, light, and hydroxylic solvents that would instantly decompose any normal silver/olefin complex. It is, however, decomposed by reducing agents to yield silver metal and recovered tetraene.105 in-Bicyclo [4.4.4]tetradecene (78), prepared by the keto aldehyde carbonyl-coupling reaction shown in entry 28, was synthesized as a precursor to m,out-bicyclo [4.4.4]tetradecane (79) and to the m-bicyclo-[4.4.4]-l-tetradecyl cation (80). This extraordinary cation, the first stable organic substance to contain a three-center, two-electron C-H-C bond, has yielded some fascinating chemistry.…”

Section: B Synthesis Of Unusual Moleculesmentioning

confidence: 99%