Helvetica Chimica Acta p. 543 - 548 (1991)
Update date:2022-09-26
Topics:
Pamingle, Herve
Snowden, Roger L.
Schulte-Elk, Karl H.
Naturally occurring (-)-(R,R)-α -necrodol ((-)-1) and its C(4)-epimer (-)-2 are obtained in 84 and 44% yields, respectively, by lithium ethylenediamide (LEDA) treatment of the corresponding β-necrodols (-)-3 and (-)-4 (Scheme I , Table), both readily available from (-)-campholenyl acetate ((-)-i) by an efficient stereoselective synthesis. The thermodynamically preferred (-)-(R)-y -necrodol ((-)-5) becomes the major product ( ≥ 80 % yield) after either prolonged treatment with LEDA or exposure of α- and β-necrodols to BF3Et2O. In an alternative route, (+)-5 is prepared starting from (+)-campholenal ((+)-ii) via Pd-catalysed decarbonylation to (-)-(S)-1,4,5,5-tetramethylcyclopent-1-ene ((-)-6) and subsequent application of an acid-catalysed CH2O-addition/ rearrangement sequence (Scheme 2).
View MoreNEW FORTUNE INDUSTRIAL CO.,LTD.
website:http://newfortune.lookchem.com/
Contact:+86-25-8645-9456
Address:C4-105 GREEN ISLAND FLOWER TOWN
CHANGYI CITY FENGRUN FINE CHEMICAL CO.,LTD
website:http://www.fengrunhuagong.com
Contact:+86-536-7869976
Address:Changyi Coastal Economic Development Zone
Jiangxi Hessence Chemicals Co., Ltd.
Contact:+86 796 3511924
Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
Zhejiang Kente Chemical Co.,Ltd.
Contact:86-0576-87651912
Address:No.7, Fengxi West Road, Modern Industrial Zone
Shanghai Potomer International Trade CO., LTD
Contact:+86-21-61397128
Address:Room 304,No.505 ,Caoyang Road.Shanghai,China
Doi:10.1021/ic201841m
(2012)Doi:10.1016/S0040-4039(00)71249-4
(1991)Doi:10.1021/ol203166c
(2012)Doi:10.1021/ic202000b
(2012)Doi:10.1246/bcsj.64.1800
(1991)Doi:10.1246/cl.2011.1363
(2011)