Vince lactam

Lonza operate a continuous process for the production of Vince lactam [23]. This is a component of the anti-HIV reverse transcriptase inhibitors, abacavir and carbovir (Scheme 11.11) [24]. Methanesulfonyl cyanide is generated in situ and reacted catalyhcally (10mol%) with cyclopentadiene in a flow process. The resulting Diels-Alder adduct is hydrolyzed to produce Vince lactam. The methanesulflnic... 

Synthesis of optically active PF-04634817 (271) based on commercially available (-)-Vince Lactam as chirality source. Starting from (-)-Vince Lactam the chiral key 4-amino-2-cyclopentene-l-carboxylic acid derivative 286 was synthesized. The componnd 286 is dimethyl pyrrole protected form of corresponding aminoacid, which was subjected to amide coupling with Boc-protected diamine 287 to give... 

In 1974, Jagt and Van Leusen (74JOC564) found that sulfonyl cyanides are good dienophiles. At room temperature, tosyl cyanide (67) dissolved in cyclopentadiene 68 is converted into 3-tosyl-2-azabicyclo [2.2.1 ]hepta-2,5-diene (69) (95%). This is the first example of the formation of a primary Diels-Alder cycloadduct of a nitrile. Adduct 69 was hydrolyzed with acetic acid and water to the lactam 70. Daluge and Vince (73JOC2311) used 70 to synthesize puromycin analog 76 (Scheme 9). Lactam 70 was hydrolyzed to the cis-amino... 

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