Stereoselective synthesis of an analog of podophyllotoxin by an intramolecular Diels-Alder reaction

…, PYS Lam, MM Mansuri, LM Speltz

Index: Jung, Michael E.; Lam, Patrick Yuk-Sun; Mansuri, Muzzamil M.; Speltz, Laurine M. Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1087 - 1105

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Citation Number: 83

Abstract

The dihydrobenzocyclobutene 90 having a 4-hydroxycrotonate unit attached via an ester linkage as an internal dienophile can be cyclized to a 3: l mixture of the trans lactone 92 (an analogue of podophyllotoxin, 1) and the cis lactone 93. This stereoselective reaction proceeds via the intermediacy of the o-quinodimethane 91 which cyclizes from the endo transition state 91n in preference to the exo-one 91x, presumably because of stabilization ...

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piperonal Structure

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piperonal

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Benzyltriphenylphosphonium bromide Structure

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2-(1,3-Benzodioxol-5-yl)-1-phenylethanone Structure

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6-Bromopiperonal Structure

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2-(1,3-Benzodioxol-5-yl)-1-phenylethanone Structure

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Benzyl bromide Structure

100-39-0

Benzyl bromide

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2-(1,3-Benzodioxol-5-yl)-1-phenylethanone Structure

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(E)-6-bromo-5-(2-phenyl-1,2-epoxyethyl)benzo-1,3-doxole Structure

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2-(1,3-Benzodioxol-5-yl)-1-phenylethanone Structure

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6-bromobenzo-1,3-dioxole-5-propanonitrile Structure

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5-cyano-5,6-dihydrocyclobuta(f)-1,3-benzodioxole Structure

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α-cyano-6-bromobenzo-1,3-dioxole-5-propanoic acid Structure

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5-cyano-5,6-dihydrocyclobuta(f)-1,3-benzodioxole Structure

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5-BROMO-6-NITROBENZO[D][1,3]DIOXOLE Structure

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5-BROMO-6-NITROBENZO[D][1,3]DIOXOLE Structure

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5-BROMO-6-IODOBENZO[D][1,3]DIOXOLE Structure

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piperonal Structure

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piperonal

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5-BROMO-6-IODOBENZO[D][1,3]DIOXOLE Structure

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6-Bromopiperonal Structure

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piperonal Structure

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piperonal

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Cyclobuta[f]-1,3-benzodioxol-5-ol, 5,6-dihydro-5-phenyl Structure

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Cyclobuta[f]-1,3-benzodioxol-5-ol, 5,6-dihydro-5-phenyl Structure

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Benzyl bromide

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Cyclobuta[f]-1,3-benzodioxol-5-ol, 5,6-dihydro-5-phenyl Structure

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piperonal Structure

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piperonal Structure

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5,8-Epoxynaphtho[2,3-d]-1,3-dioxole, 5,8-dihydro Structure

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5,8-Epoxynaphtho[2,3-d]-1,3-dioxole, 5,8-dihydro Structure

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5-amino-6-bromobenzo-1,3-dioxole hydrochloride Structure

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5,8-Epoxynaphtho[2,3-d]-1,3-dioxole, 5,8-dihydro Structure

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