207680-79-3

Upstream product

• 93-97-0 benzoic acid anhydride 
• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 
• 160666-92-2 (S)-2-benzoyloxypentan-3-one 
• 125948-63-2 (S)-2-hydroxypentan-⁽³⁾-one 

Downstream Products

• 207680-83-9 (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one 
• 888488-17-3 (3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one 
• 888488-07-1 (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione 
• 888488-15-1 (3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-3-(p-methoxybenzyloxy)-4,6-dimethylheptane 
• 888488-34-4 (2R,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptan-1-ol 
• 888488-09-3 (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal 
• 888488-14-0 (3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-ol 
• 888488-12-8 (4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one 
• 207680-86-2 (2S,3R,4S,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-2,3-diol 

Relevant academic research and scientific papers

Truncated Actin-Targeting Macrolide Derivative Blocks Cancer Cell Motility and Invasion of Extracellular Matrix

Cancer metastasis is a complex process involving highly motile tumor cells that breach tissue barriers, enter the bloodstream and lymphatic system, and disseminate throughout the body as circulating tumor cells. The primary cellular mechanism contributing to these critical events is the reorganization of the actin cytoskeleton. Mycalolide B (MycB) is an actin-targeting marine macrolide that can suppress proliferation, migration, and invasion of breast and ovarian cancer cells at low nanomolar doses. Through structure-activity relationship studies focused on the actin-binding tail region (C24-C35) of MycB, we identified a potent truncated derivative that inhibits polymerization of G-actin and severs F-actin by binding to actin's barbed end cleft. Biological analyses of this miniature MycB derivative demonstrate that it causes a rapid collapse of the actin cytoskeleton in ovarian cancer cells and impairs cancer cell motility and invasion of the extracellular matrix (ECM) by inhibiting invadopodia-mediated ECM degradation. These studies provide essential proof-of-principle for developing actin-targeting therapeutic agents to block cancer metastasis and establish a synthetically tractable barbed end-binding pharmacophore that can be further improved by adding targeting groups for precision drug design.

CYTOTOXIC ACTIN-TARGETING COMPOUNDS

A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition

A retro-Claisen approach to dolabriferol

The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone

Polyketide synthesis using the boron-mediated, anti-aldol reactions of lactate-derived ketones: Total synthesis of (-)-ACRL toxin IIIB

The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reag