88155-83-3

Upstream product

• 37555-63-8 dibromomethyllithium 
• 82414-47-9 (E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 87763-64-2 (2S,3R)-2-Methoxy-3-methyl-pent-4-enoic acid methyl ester 
• 67498-12-8 (E)-syn-methyl 3-hydroxy-2-methyl-5-phenyl-4-pentanoate 
• 67498-12-8 (E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester 
• 86853-06-7 Methyl 2-methyl-3-oxo-5-phenyl-4-pentenoate 
• 82414-51-5 (E)-(2S,3S)-2-Methyl-5-phenyl-pent-4-ene-1,3-diol 
• 14371-10-9 (E)-3-phenylpropenal 
• 106315-57-5 (3R,4S)-1-(Diphenyl-phosphinoyl)-3-methoxy-4-methyl-1-phenyl-hex-5-en-2-one 
• 88088-52-2 (3R,4S)-4-Methyl-1-phenyl-hex-5-en-1-yn-3-ol 
• 79705-07-0 (3S,4R)-4-Methyl-hex-5-en-1-yn-3-ol 
• 84118-90-1 (syn)-(E)-3-hydroxy-4-methyl-1-phenyl-1,5-hexadiene 
• 106315-57-5 1-(Diphenyl-phosphinoyl)-3-methoxy-4-methyl-1-phenyl-hex-5-en-2-one 
• 88088-54-4 (E)-(3S^*,4R^*)-3-methoxy-4-methyl-1-phenylhexa-1,5-diene 

Downstream Products

• 73341-71-6 (+/-)-oudemansin A 
• 73341-71-6 oudemansin A 
• 109864-20-2 (E)-(3S,4S)-2-[1-Hydroxy-meth-(Z)-ylidene]-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester 
• 90664-08-7 (E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF OUDEMANSINS A AND B

Efficient, stereocontrolled syntheses of the antifungal metabolites oudemansin A and B are described.

-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM; AN EMERGING TOOL FOR CONTROL OF ACYCLIC STEREOCHEMISTRY

The -Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds.Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (+/-)-oudemansin.Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond.

ENHANCEMENT OF ERYTHRO-SELECTIVITY IN THE -WITTIG REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM AND ITS USE IN THE STEREOCONTROLLED FORMAL SYNTHESIS OF (+/-)-OUDEMANSIN

The -Wittig variant of (Z)-crotyl ether involving trimethylsilylethynyl (or 1-propynyl) group as the key substituent on the carbanion terminus exhibits an exceptionally high level of erythro-selection, and its synthetic potential is illustrated in th