228419-58-7

Upstream product

• 319922-89-9 (2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-hex-en-1-ol 
• 319922-31-1 (2R,3R,4R)-1,3-O-(4-methoxy-benzylidene)-4-(tert-butyldimethylsilanyloxy)-2,5-dimethyl-hex-5-en 
• 228419-55-4 (Z)-γ-(tert-butyldimethylsilanyloxy)methallyltributylstannane 
• 228419-57-6 (2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-hex-5-en-3-ol 
• 160238-46-0 (2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal 

Relevant academic research and scientific papers

Synthesis of the C(29)-C(45) bis-pyran subunit (E-F) of spongistatin 1 (altohyrtin A)

A synthesis of the C(29)-C(45) bis-pyran subunit 2 of spongistatin 1 (1a) is described. The synthesis proceeds in 19 steps from the chiral aldehyde ent-7, and features highly diastereoselective α-alkoxyallylation reactions using the γ-alkoxy substituted allylstannanes 17 and 19, as well as a thermodynamically controlled intramolecular Michael addition to close the F-ring pyran. The E ring was assembled via the Mukaiyama aldol reaction of F-ring methyl ketone 3 and the 2,3-syn aldehyde 4.