180780-69-2

Upstream product

• 180780-67-0 [(1S,2S,3R)-2,3-Bis-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethyl-butyl]-dimethyl-amine 
• 180780-68-1 (2R,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentan-1-ol 

Downstream Products

• 180780-60-3 (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate 
• 180780-71-6 (2S,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentanoic acid [(1R,3S)-3-(4-chloromethyl-oxazol-2-yl)-1-methyl-butyl]-amide 

Relevant academic research and scientific papers

Asymmetric synthesis of calyculin C. 2. Synthesis of the C26-C37 fragment and model Wittig couplings

We report our synthesis of the C26-C37 fragment of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C (1). Outlined in this paper are synthetic approaches to the two components based on disconnection at the C33-N3 amide bond. We report the successful synthesis of the C33-C37 aza-sugar derived from D-lyxose which was coupled onto a C26-C32 aminooxazole originating from L-pyroglutamic acid. Elaboration of the resulting amide to a fully deprotected C26-C37 fragment of calyculin C completed our synthesis. This provided an appropriate phosphonium salt for use in a Wittig olefination for joining both halves of the natural product.