Expedient Synthesis, on Large Scale, of Aliphatic Chaetomellic Anhydrides from N-Allyl-2,2-dichlorocarboxyamides

TY - JOUR

T1 - Expedient Synthesis, on Large Scale, of Aliphatic Chaetomellic Anhydrides from N-Allyl-2,2-dichlorocarboxyamides

AU - Ghelfi, Franco

AU - Pattarozzi, Mariella

AU - Roncaglia, Fabrizio

AU - Giangiordano, Valerio

AU - Parsons, Andrew F.

PY - 2010/1

Y1 - 2010/1

N2 - Chaetomellic anhydride A and an analog (with two additional carbons) were obtained, on a preparative scale, starting from amides derived from the acylation of 2-(2-propenylamino)pyridine with 2,2-dichloropalmitic or 2,2-dichlorostearic acid. An alternative approach, in which the methyl substituent of the target anhydride is introduced by the carboxylic acid reactant and the long aliphatic chain is added through the allylamino moiety, proved unviable.

AB - Chaetomellic anhydride A and an analog (with two additional carbons) were obtained, on a preparative scale, starting from amides derived from the acylation of 2-(2-propenylamino)pyridine with 2,2-dichloropalmitic or 2,2-dichlorostearic acid. An alternative approach, in which the methyl substituent of the target anhydride is introduced by the carboxylic acid reactant and the long aliphatic chain is added through the allylamino moiety, proved unviable.

KW - Chaetomellic anhydride

KW - halocompounds

KW - lactams

KW - radical reactions

KW - FARNESYL-PROTEIN TRANSFERASE

KW - FUNCTIONAL REARRANGEMENT

KW - ACIDS

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=77749298114&partnerID=8YFLogxK

U2 - 10.1080/00397910903029974

DO - 10.1080/00397910903029974

M3 - Article

SN - 0039-7911

VL - 40

SP - 1040

EP - 1051

JO - SYNTHETIC COMMUNICATIONS

JF - SYNTHETIC COMMUNICATIONS

IS - 7

ER -