117202-94-5

Upstream product

• 107-39-1 2,4,4-trimethyl-1-pentene 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 999-78-0 4,4-dimethyl-2-pentyne 
• 201230-82-2 carbon monoxide 
• 147227-25-6 α,α-bis(trimethylsilyl)-tert-butylpropionaldimine 
• 630-19-3 pivalaldehyde 
• 22147-70-2 ethyl (2E)-2,4,4-trimethyl-2-pentenoate 
• 81171-61-1 methyl (E)-2,4,4-trimethylpent-2-enoate 
• 51483-32-0 (2E)-2,4,4-trimethylpent-2-en-1-ol 

Downstream Products

• 17414-46-9 2,4,4-trimethylpentanal 
• 272121-01-4 (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester 
• 272121-08-1 (6E,8E)-(4S,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester 
• 272121-04-7 (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl(2R,3R,4E,6E)-3-triethylsiloxy-2,4,6,8,8-pentamethyl-4,6-nonadienoate 
• 272120-89-5 (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl(2S,3S,4E,6E)-3-triethylsiloxy-2,4,6,8,8-pentamethyl-4,6-nonadienoate 
• 272121-00-3 (3S,4R,5S)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide 
• 222547-87-7 (6E,8E)-(4R,5R)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester 
• 222547-85-5 (4R,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide 
• 218778-75-7 (6E,8E)-(3R,4S,5R)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester 
• 1026867-78-6 (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester 
• 218778-52-0 [4R,3(2R,3R)]-4-benzyl-3-(3-hydroxy-2,4,6,8,8-pentamethyl-4,6-nonadienoyl)-2-oxazolidinone 
• 218778-72-4 (3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide 

Relevant academic research and scientific papers

Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.

Enantioselective Allylation of β-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin

A comparative study of the catalytic allylations and crotylations of (E)- and (Z)-haloacrylaldehydes by Lewis bases (chiral N,N′-dioxides) and Br?nsted acids (chiral phosphoric acids) was undertaken. The reactions proceeded with high enantio- and diastereoselectivities with slightly better asymmetric induction observed in the case of N,N′-dioxide catalysis. The formed enantioenriched chiral unsaturated haloalcohols could be considered general building blocks, as they could be used in the syntheses of more complex natural products possessing substituted 1,3-diene fragments. This was exemplified by the formal total syntheses of pteronenone and antillatoxin. A comparative study of allylations and crotylations of (E)- and (Z)-haloacrylaldehydes is undertaken under Lewis base and Br?nsted acid catalysis. The reactions proceed in both cases with high enantio- and diastereoselectivities. The formed chiral unsaturated haloalcohols can be considered as general building blocks, as exemplified by the formal total syntheses of pteronenone and antillatoxin; HBPin = pinacolborane.

Selective palladium-catalyzed hydroformylation of alkynes to α,β-Unsaturated Aldehydes

Atom-efficient: A selective palladium catalyst system is used for the hydroformylation of alkynes (see picture). In this syngas reaction, various alkynes were smoothly transformed to synthetically interesting α,β-unsaturated aldehydes in good yields with high regio- and stereoselectivity. Copyright

Total synthesis of antillatoxin

The total synthesis of natural (4R,5R)-antillatoxin and its analog (4S,5S)-antillatoxin has been achieved; the optically pure key intermediates were prepared from indium mediated allylation of either primary or secondary allylic bromide with aldehyde in a

A general route to α-alkyl (E)-α,β-unsaturated aldehydes

Bis(trimethylsilyl)-tert-butylaldimines 3 react with aldehydes in the presence of zinc bromide at room temperature to give, after hydrolysis, the desired α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity. The reaction was believed to proceed via the α-silyl β-siloxyimines 4.

Total synthesis and revision of absolute stereochemistry of antillatoxin, an ichthyotoxic cyclic lipopeptide from marine cyanobacterium Lyngbya majuscula

Antillatoxin is an ichthyotoxic cyclic lipopeptide isolated by Gerwick and co-workers from the marine cyanobacterium Lyngbya majuscula collected in Curacao. Although we have finished the stereoselective total synthesis of antillatoxin having the proposed structure with (4S,5R)-configuration, we have found that the synthetic sample was not identical with the natural one and the proposed structure should be revised. Further our synthetic efforts have culminated in the first total synthesis of antillatoxin in its natural form, proving that the natural one has (4R,5R)-configuration. (C) 2000 Elsevier Science Ltd.

Rhodium-katalysierte Hydroformylierung innerer Alkine zu α,β-ungesaettigten Aldehyden

Keywords: Alkine; Hydroformylierungen; Katalyse; Alkene; Rhodiumverbindungen

Photooxygenation of olefins in the presence of titanium(IV) catalyst: A convenient 'one-pot' synthesis of epoxy alcohols

The photooxygenation of olefins in the presence of transition-metal complexes derived from Ti, V, and Mo constitutes a convenient and efficient 'one-pot' synthesis of epoxy alcohols. First, singlet oxygen transforms the olefin via an ene reaction into its allylic hydroperoxide, and subsequently, the allylic hydroperoxide is converted via transition-metal-catalyzed oxygen transfer into its epoxy alcohol. From the point of view of the olefinic substrate, the oxygen transfer is intermolecular, one allylic hydroperoxide molecule serving as oxygen donor and the other as oxygen acceptor in the form of its allylic alcohol, the transition metal playing the role of a template for both as in the Sharpless epoxidation. Unlike the latter process, the hydroperoxide donor and the allylic alcohol acceptor are generated in situ and continually consumed via a novel oxygen-transfer chain sequence.