19078-37-6Relevant articles and documents
A stereoselective synthesis of (±)-C-secolimonoid BCDE model compounds related to the insect antifeedant ohchinolide
Fernandez Mateos,Martin de la Nava,Rubio Gonzalez
, p. 7632 - 7638 (2001)
A short and stereoselective synthesis of (±)-BCDE C-secolimonid model insect antifeedant related to ohchinolide and nimbolidin was accomplished in 13 (30% overall yield and 15 (30% overall yield) steps, respectively, from ethyl drimanate. The key steps are the torquoselective electrocyclization of the divinyl ketone 6, induced by perchloric acid, and the stereoselective rearrangement of the hydroxy lactone 12, inspired in a biosynthetic proposal. An alternative route, which provides access to (±)-BCDE ohchinolide and nimbolidin isomers, is also described.
A NEW OLEFIN CYCLIZATION AGENT, MERCURY(II) TRIFLUOROMETHANESULFONATE-AMINE COMPLEX
Nishizawa, Mugio,Takenaka, Hideyuki,Nishide, Hisaya,Hayashi, Yuji
, p. 2581 - 2584 (1983)
A new reagent, mercury(II) trifluoromethanesulfonate-amine complex, has been developed for effective cyclization of various farnesol derivatives in good yield and high selectivity.
STRUCTURE-SELECTIVE STEREOSPECIFIC CYLCIZATION OF E,E-FARNESOL AND ITS ACETATE BY FLUOROSULFONIC ACID
Vlad, P. F.,Ungur, N. D.,Perutskii, V. B.
, p. 737 - 738 (1986)
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Superacid cyclization of certain aliphatic sesquiterpene derivatives in ionic liquids
Grin'ko,Kul'chitskii,Ungur,Vlad
, p. 439 - 441 (2008/02/07)
Superacid cyclization was demonstrated for the first time to be successful in those ionic liquids with functional groups that are stable in the reaction medium using aliphatic sesquiterpene derivatives as examples.
A convenient synthesis of (+)-albicanol based on enzymatic function: Total syntheses of (+)-albicanyl acetate, (-)-albicanyl 3,4- dihydroxycinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox
Akita, Hiroyuki,Nozawa, Masako,Mitsuda, Ayumi,Ohsawa, Hitomi
, p. 1375 - 1388 (2007/10/03)
By using lipase 'PL-266' from Alcaligenes sp. enantioselective acetylation of (±)-albicanol 4 with isopropenyl acetate gave the enantiomerically pure (+)-albicanyl acetate 3 and (+)-albicanol 4. Deprotection of (+)-3 afforded the natural (+)-albicanol 4 which was converted to the natural products (-)-albicanyl 3,4-dihydroxycinnamate 7, (- )-drimenol 8, (-)-drimenin 9 and (-)-ambrox 10. (C) 2000 Elsevier Science Ltd.