Total Synthesis of Sarcophytol A, an Anticarcinogenic Marine Cembranoid

Autor:	Hisao Takayanagi, Yasuhiro Morinaka, Yasunori Kitano
Rok vydání:	1994
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone chemistry Intramolecular reaction Nitrile Organic Chemistry Enantioselective synthesis Organic chemistry Total synthesis Ether Alkylation Cyanohydrin
Zdroj:	The Journal of Organic Chemistry. 59:2700-2706
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00089a011
Popis:	A highly stereo- and enantioselective total synthesis of sarcophytol A (1), a marine cembranoid promising as a cancer chemopreventive agent, is described. The nitrile 10 obtained Z-selectively (Z:E=>35:1) by the Horner-Emmons reaction of (E,E)-farnesal (5) with the phosphononitrile 9 in 91% yield was converted to the conjugated 2(Z),4(E)-dienal 3 in which the terminal (E)-methyl group was functionalized. Intramolecular alkylation of the cyanohydrin TMS ether of 3 provided the macrocyclic ketone 2 in 79% of overall yield from 3 without isolation of the cyclic cyanohydrin 20 as well as its TMS ether 19. Reduction of 2 with several chiral LiAlH 4 reagents afforded 1 highly enantioselectively (78-97%) yield, from which enantiomerically pure 1 (>99% ee) was readily obtained upon a single recrystallization
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c11af3b812acde783a302db1f1875e02 https://doi.org/10.1021/jo00089a011