Patent ID: 7183417
Filing Date: 2007-02-27
Classification: C07C,C07D,C07F

Abstract:
1. A process for the enantiospecific total synthesis of the compound of structure 1: comprising the steps of: (a) converting amide 3 to oxazoline 4: (b) deprotonating 4 followed by alkylation of the resulting enolate to provide 5: (c) reducing 5 to yield the N-4-methoxybenzylamine 6: (d) acylating 6a (structure not shown, OH in 6 is OTMS) to afford the N-acrylyl-N-PMB derivative 7: (e) oxidizing 7 to produce the keto amide ester 8: (f) cyclizing 8 to afford the γ-lactam 9: (g) silylating 9 to produce the silyl ether 11: (h) cyclizing 11 to provide the cis-fused γ-lactam 12: (i) cleaving the protecting group (OBn) in compound 12 to yield the primary alcohol 12a (wherein OBn in 12 is OH), and oxidizing 12a to provide the aldehyde 13: (j) reacting 2-cyclo-hexenyizine chloride with the aldehyde 13 to yield the formyl adduct 14: (k) oxidizing 14 to provide the triol 15: (l) cleaving the PMB group of 15 to yield the triol ester 16: (m) hydrolyzing 16 to the corresponding γ-lactam-carboxylic acid 16a (CO