By Gould R.F. (ed.)

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PCC, CH2CI2,2 h O 1 19 95% 98 4-epibakkenolide-A MeO 97 Bu3snCl(cat') NaCNBH3 _--. 5h 83% "" 99 Intramolecular cyclization of the acetal derived from propargyl alcohol 100 under reductive conditions gave the acetal 101 in high yield [95SL893]. Compound 102 has been converted to (3S, 4R)-luffariolide E. P " ~ r OCHPh2 101 \/ I , II / ~ ] fH 102 (3S,4R)-LuffariolideE Radical cyclization with iodine atom transfer of a highly functionalized propiolic ester 103 using dibenzoyl peroxide as an initiator gave the a-methylene-~,-butyrolactone 104 in good yield [95T11257].

SPh Bu3SnH,AIBN toluene, reflux 97% ~ N" . 13:(+)-Continine The addition of sulfur radicals to isocyanides produces imidoyl radicals as intermediates. The stereocontrolled 5-exo-trig cyclization of imidoyl radicals in the synthesis of substituted (alkylthio)pyrrolines, pyroglutamates, and thiopyroglutamates has been reported [95JOC6242]. The intermediate 137 is not isolated but undergoes further thermal reaction to furnish a pyroglutamate derivative. Synthesis of Heterocyclic Compounds 28 N~OTBDMS IC H O / ~ / S H c o 2 E t AIBN,80 ~ 82% __I~OTBDMS S'~N"LCO2 Et HO,v,,J 135 136 J,% O"T "N" BDM '" S s = ~CO2Et HO,v,,J 137 Intramolecular cyclization of N-alkenyl-2-bromoindoles has been described.

The product ratio has some dependency on the nitrogen ligand used with the samarium species. I / sm2,H , M4h PA 71% 130 I ,sH2ooc + 131 131:132= 81:19 132 Synthesis of pyrrolidin-2-ones by cyclization through the generally disfavored 5-endo-trig mode has been reported [95JCS(P1)ll15]. Treatment of the disulfanyl acetal 133 under reductive conditions furnished continine 134, a nicotine metabolite in high yield. Reaction of the corresponding dichloro or monochloro compound gave none or very small amounts of the cyclized compounds.

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