671782-82-4

Upstream product

• 476365-41-0 methylketene dimer 
• 27970-79-2 (R)-2-Methyl-3-oxopentanol 
• 19790-60-4 3-Benzyloxypropanal 
• 671782-79-9 3,4-dimethoxybenzoic acid (2R)-2-methyl-3-oxopentyl ester 

Downstream Products

• 725251-02-5 (E)-(2R,4R,8S,11R)-11-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2,8-dimethoxy-4,7-dimethyl-dodec-6-enal 
• 725250-92-0 {(R)-5-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-methyl-2-oxo-hexyl}-phosphonic acid diethyl ester 
• 725250-90-8 3,4-Dimethoxy-benzoic acid (R)-2-[(4R,5R,6R)-6-(2-benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester 
• 725250-91-9 (4R,5R,6S)-4-(2-Benzyloxy-ethyl)-6-((S)-2-iodo-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxane 

Relevant academic research and scientific papers

Catalytic, Asymmetric Synthesis and Diastereoselective Aldol Reactions of Dipropionate Equivalents

The dimer of methylketene can be conveniently prepared in one step and high enantiomeric excess from propionyl chloride, using a catalytic amount of a silylated cinchona alkaloid as a source of chirality. Opening of the dimer with a lithiated sulfonamide

Synthesis of the C1-C27 portion of the aplyronines

This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C5-C14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C15-C20 of the targets. Further elaboration and an additional coupling led to an intermediate containing C1-C27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines.