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Design, synthesis, and evaluation of analogues of (+)-14-normethyldiscodermolide
Journal article   Peer reviewed

Design, synthesis, and evaluation of analogues of (+)-14-normethyldiscodermolide

Amos B Smith, 3rd, B Scott Freeze, Matthew J Lamarche, Tomoyasu Hirose, Ignacio Brouard, Ming Xian, Kurt F Sundermann, Simon J Shaw, Mark A Burlingame, Susan Band Horwitz, …
Organic letters, Vol.7(2), pp.315-318
01/20/2005
DOI: https://doi.org/10.1021/ol0476873
Handle:
https://hdl.handle.net/2376/105503
PMID: 15646986

Abstract

Antineoplastic Agents - chemical synthesis Humans Structure-Activity Relationship Antineoplastic Agents - chemistry Pyrones - pharmacology Carbamates - chemistry Alkenes - chemistry Carbamates - chemical synthesis Pyrones - chemistry Cell Line, Tumor Inhibitory Concentration 50 Antineoplastic Agents - pharmacology Molecular Structure Pyrones - chemical synthesis Carbamates - pharmacology Lactones - chemistry
[Structure: see text] The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (+)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.

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