910789-75-2

Upstream product

• 147782-81-8 (2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 81790-10-5 (2-bromoallyl)trimethylsilane 
• 3587-60-8 Benzyloxymethyl chloride 
• 910789-72-9 (3S,4S,6R)-7-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-trimethylsilanylmethyl-hept-1-en-3-ol 
• 910789-71-8 (4S,6R)-7-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-trimethylsilanylmethyl-hept-1-en-3-one 
• 910789-73-0 (2R,4S,5S)-2,4-Dimethyl-6-trimethylsilanylmethyl-hept-6-ene-1,5-diol 
• 910789-74-1 [(1S,2S,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-1-(1-trimethylsilanylmethyl-vinyl)-pentyloxymethoxymethyl]-benzene 

Relevant academic research and scientific papers

Synthesis of open-chain C21-C40 fragment of azaspiracid-1

Here, we report a synthesis of a differentially protected, open-chain C21-C40 fragment of azaspiracid-1, corresponding to the lower half EFGHI-ring domain. The synthesis features modular coupling of three advanced intermediates, aiming for diverted analogue synthesis. A new method for construction of E-ring moiety amenable to the diverted synthesis is also reported.

Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment

Here, we report a synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1. The C28-C 40 fragment was synthesized by a coupling between the C 28-C35 epoxide and the C36-C40 dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C28-C40 fragment was then coupled with the C21-C27 allylic stannane by using InCl 3. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C21-C40 fragment.