25406-65-9

Upstream product

• 80325-27-5 (7R,8R,9S)-9-Acetoxymethyl-2,4,10-trioxa-tricyclo[5.3.1.0^3,8]undec-5-ene-6-carboxylic acid methyl ester 
• 80325-31-1 (4aR,6S,8S,8aR)-8-Acetoxymethyl-1-hydroxy-6-methoxy-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 
• 80325-26-4 (4aR,6S,8S,8aR)-1-Hydroxy-6-methoxy-8-trityloxymethyl-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 
• 80325-30-0 (1R,4aR,6S,8S,8aR)-1-Acetoxy-6-methoxy-8-trityloxymethyl-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 
• 50427-65-1 2-Formyl-3-oxo-propionsaeure-methylester 
• 80584-54-9 (2S,6R)-2-Methoxy-6-methyl-3,6-dihydro-2H-pyran 
• 118598-33-7 methyl (+/-)-<1R*,5S*,7R*,9S*(S*)>-7-hydroxy-9-(1-methoxyethyl)-2,8-dioxabicyclo<3.1.1>non-3-ene-4-carboxylate 
• 118598-26-8 methyl (+/-)-(E)-α-(2-phenylethenyl)-2-(1-hydroxyethyl)-3-cyclopentene-1-ethanoate 
• 118598-19-9 7-methyl-6-oxabicyclo<3.2.0>hept-2-ene 
• 118598-23-5 dimethyl (+/-)-<1α,2β(R*)>-(E)-<2-(1-methoxyethyl)-3-cyclopentenyl>(2-phenylethenyl)propanedioate 
• 118598-21-3 (+/-)-<1α,2α(S*)>-2-(1-methoxyethyl)-3-cyclopentenyl 4-methylbenzenesulfonate 
• 118598-25-7 methyl (+/-)-(E)-α-(2-phenylethenyl)-2-(1-methoxyethyl)-3-cyclopentene-1-ethanoate 
• 118598-24-6 (E)-2-[(1S,2S)-2-((S)-1-Methoxy-ethyl)-cyclopent-3-enyl]-4-phenyl-but-3-enoic acid 
• 118598-20-2 (+/-)-<1α,2α(S*)>-2-(1-methoxyethyl)-3-cyclopenten-1-ol 

Relevant academic research and scientific papers

Total synthesis of (±)-sarracenin

A total synthesis of (±)-sarracenin (1) is described. The key steps include (1) regioselective ring expansion of 7 to bicyclo[3.2.1]ketone 6 and (2) ring opening of tricyclic ketone 5 to ester 4.

A Short, Oxetane-Based Synthesis of (+/-)-Sarracenin

(+/-)-Sarracenin (1) was synthesized in nine steps and six pots from simple precursors acetaldehyde and cyclopentadiene.Paterno-Buechi photocycloaddition of this pair yielded two diastereomeric oxetanes (3x, 3n).The major, exo isomer underwent highly regioselective acid-catalyzed methanolysis at the methyl-bearing oxetane center to give a 3-cyclopentenol derivative (8).Attachment of a methyl 2-(2-phenylethenyl)ethanoate moiety, a 3-oxopropanoate equivalent, with inversion of the toluenesulfonate 9 derived from 8 gave a diene (11) containing all of the necessary carbon atoms.Following decarbomethoxylation, both olefins were simultaneously ozonized to an in situ equivalent of trialdehyde (2) which has played a role in previous synthetic studies and biosynthetic postulates in this area.Spontaneous dehydration of 2 produced (+/-)-sarracenin in 18percent overall yield from the tosylate 9, the first purified intermediate in the sequence.