6790-85-8

Upstream product

• 109585-68-4 (3E,7E)-3,7-dimethyl-oxa-3,7-cyclotridecadien-11-yne 
• 113725-52-3 (+)-(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol 
• 113680-90-3 (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate 
• 113725-50-1 (-)-(1S,2S)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol 
• 113725-53-4 (+)-(1R,2S)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol 
• 113725-54-5 (1S,2S)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate 
• 201230-82-2 carbon monoxide 
• 114027-91-7 (2Z,6E)-(1R,10S)-3-Iodo-10-isopropenyl-7-methyl-cyclodeca-2,6-dienol 
• 109585-69-5 rel-(1S,2S)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol 
• 109585-72-0 (2Z,6E)-(1S,10S)-3-Iodo-10-isopropenyl-7-methyl-cyclodeca-2,6-dienol 
• 109585-70-8 Benzoic acid (E)-(1R,10S)-10-isopropenyl-7-methyl-cyclodec-6-en-2-ynyl ester 
• 109585-83-3 (3Z,7E)-3,7-dimethyl-1-oxa-3,7-cyclotridecadien-11-yne 
• 109585-69-5 rel-(1S,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol 
• 109585-72-0 (2Z,6E)-(1S,10R)-3-Iodo-10-isopropenyl-7-methyl-cyclodeca-2,6-dienol 

Downstream Products

• 104613-44-7 (1Z,4R,5E,8S,9S)-4-hydroxy-5-methyl-8-(1-methylethenyl)-10-oxabicyclo[7.2.1]dodeca-5,12-dien-11-one 
• 104613-44-7 (1Z,4S,5Z,8S,9S)-4-hydroxy-5-methyl-8-(1-methylethenyl)-10-oxabicyclo[7.2.1]dodeca-5,12-dien-11-one 

Relevant academic research and scientific papers

Enantioselective synthesis of macrocyclic propargylic alcohols by [2,3] Wittig ring contraction. Synthesis of (+)-aristolactone and cembranoid precursors

The use of chiral lithium amide bases to initiate enantioselective [2,3] Wittig rearrangements of allylic ethers was investigated. The 13-membered propargylic ether 1, a nonresolvable racemate, afforded the 10-membered propargylic alcohol SS2 in 60-80% ee

ENANTIOSELECTIVE WITTIG RING CONTRACTION INDUCED BY CHIRAL BASES. THE TOTAL SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-ARISTOLACTONE

Wittig ring contraction of the achiral 13-membered acetylenic ether 1 via treatment with lithio (R,R) or (S,S)-bis-(1-phenylethyl)amide afforded the (R)-(+) or (S)-(-)-propargylic alcohol (+)-2 or (-)-2, respectively, of >60percent ee in 75percent yield.

TOTAL SYNTHESIS OF THE GERMACRANOLIDE (+/-)-ARISTOLACTONE VIA WITTIG RING CONTRACTION

The total synthesis of (+/-)-aristolactone (15) is described wherein the key cyclodecenynol precursor 10 is prepared in over 90 percent yield via a highly regio and stereoselective Wittig reaarangement of the 13-membered propargylic ether 9.

Stereoselective Total Synthesis of (+/-)-Aristolactone and (+/-)-Epiaristolactone via (2,3) Wittig Ring Contraction

The germacranolide bridged lactone aristolactone (16) has been synthesized starting from geranyl acetate.Homologation of derived chloride 5 via coupling with magnesium bromide followed by deprotection, metalation and addition

SYNTHESIS OF AN ISOMER OF THE GERMACRANOLIDE ISOARISTOLACTONE

Photocycloaddition of (+)-isopiperitenone and cyclobutene-1-carboxylic acid gives an adduct which upon reduction with NaCNBH3 followed by thermolysis yields an isomer of isoaristolactone in an overall yield of 26percent.